CC BY
35
2014
ВЕСТНИК САНКТ-ПЕТЕРБУРГСКОГО УНИВЕРСИТЕТА
Сер. 4. Том 1 (59). Вып. 4
ХИМИЯ
УДК 612.396.14 S. Jarosz
APPLICATION OF SUGARS IN STEREOSELECTIVE SYNTHESIS. WHAT IS INTERESTING ABOUT SUCROSE?*
Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
The review contains the information about the synthesis of higher carbon sugars, bicyclic sugar mimetics and macrocyclic derivatives with sucrose scaffold. The data of the complexation of chiral amines by these sucrose receptors are also provided. The research on sucrose chemistry helps successfully for the realization of project — "Sugars as raw materials for the preparation of compounds with high added value". Refs 74.
Keywords: sucrose, stereoselectivity, synthesis, sugar mimetics.
С. Ярош
ПРИМЕНЕНИЕ САХАРОВ В СТЕРЕОСЕЛЕКТИВНОМ СИНТЕЗЕ. ЧТО ИНТЕРЕСНОГО В САХАРОЗЕ?
Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
Обзор содержит информацию о синтезе высших сахаров, бициклических сахаро-миметиков, макроциклических сахаро-рецепторов и включает данные о комплексующих свойствах и сахарных макроциклических производных. Исследования химии сахарозы помогают успешной реализации проекта «Сахара как исходные материалы для соединений с исключительными дополнительными свойствами». Библиогр. 74 назв.
Ключевые слова: сахароза, стереоселективный синтез.
Dedicated to Professor Mieczyslaw Makosza on the occasion of his 80th birthday
I. Introduction. This paper will be a kind of an account describing my work in the Institute of Organic Chemistry, PAS and the influence of Professor Mieczyslaw Makosza on my research career. The field of my work is stereochemistry with special attention to sugars, so I am far away from the chemistry of aromatic compounds which Prof. Makosza "likes a lot".
My independent career started after habilitation in 1990 dedicated to higher carbon sugars (HCS), i. e. monosaccharides with more than ten carbon atoms in the chain. That
* The support from Grant: POIG.01.01.02-14-102/09: "Sugars as raw materials for the preparation of compounds with high added value" (part-financed by the European Union within the European Regional Development Fund) is acknowledged.
time this was a very "fresh" subject and only limited number of papers describing the preparation or isolation of these complex derivatives were reported in the literature [1-10]; in 1990s this area received more significant interest [11-16].
I have proposed to continue my research on HCS to the Director of IOC PAS, Prof. Makosza. Since HE was not a passionate of sugars, he refused to accept my proposal. But the conclusion was: if Jarosz is really interested in sugars, he should try to do (something) with sucrose! So I have started my independent career which was focused on sucrose, doing also other type of chemistry in which sugars were used as chirons. The material presented in this account will briefly show my research interest in sugar chemistry with the special attention to, strongly suggested by Prof. Makosza, sucrose.
II. Synthesis of higher carbon sugars. I joined sugar chemistry field in the beginning of 1980's working as a post-doc with Prof. Bert Fraser-Reid at the University of Maryland in College Park (USA). We proposed the useful synthesis of higher carbon sugars (e. g. enone 5) by a Wittig reaction of sugar phosphorane and sugar aldehyde; the idea is shown in Scheme (1) (route a) [17]. Since the preparation of stabilized Wittig reagents (e. g. 3) can be capricious I proposed later to replace them with phosphonates (6; route b in Scheme (1)) [18, 19].
By this strategy, higher carbon sugars of different size were synthesized; a leading example of such complex product is C21 HCS enone 7 shown in Scheme (2), prepared by us in mid-1990's [20]; this research was summarized in a review [21].
Bna OBnOBnOBn BnO, " '
BnO\O OBn OBn "OBn MeO
(2)
7
BnO T "OBn
OBn
We found that higher sugar enones with "reasonable high size" (12-13 carbon atoms in the chain) could be highly stereoselectively reduced with zinc borohydride [22]. For example, treatment of enone 8 with Zn(BH4)2 provided higher sugar allylic alcohol 9, with the R configuration at the newly created stereogenic center, as the only product (Scheme (3)). This was explained assuming the cyclic model 10 in which the zinc cation was complexed to the carbonyl and the ring oxygen atoms fixing the conformation; the attack of hydride anion
occurred, therefore, from the less hindered side of the molecule (from "the bottom") [23].
Higher sugar skeleton was also prepared from sugar acetylenes [24]. For example, compound 11 was, under the basic conditions, converted into anion which reacted with sugar aldehyde providing propargylic alcohol 13, direct precursor of the Z-olefin 14. Alternatively, semi-reduction of the triple bond in 11 with tin hydride afforded vinyltin intermediate 12 (equivalent of vinyl anion) which, by reaction with sugar aldehyde, yielded S-alcohol 15. This enabled us to propose the convenient synthesis of HCS alcohols as shown in Scheme (4) [25].
O
f Sug
1. BuLi
2. Sug1-CHO
Sug 11
Sug
^OH ~13 Sugi
SnBu i 3 ^CH
Sug 12 \
1. BuLi
2. Sug1-CHO
Lindlar
Su
14
OH
Sugi
(4)
Sug
15
OH
* Sug1
Bu3SnH
Combination of the two approaches (i. e. phosphorane and acetylene) allowed us to propose an effective and relatively short synthesis of HCS; the idea is shown in Scheme (5). For example, preparation of enone 19, composed of two monosaccharide units (ribose and galactose), could be initiated from "either end" (a: "vinyltin route" from ribose or b: "phos-phorane route" from galactose) depending on the availability of the starting material [26].
Why not to try another opportunity to connect two sugar units together? Application of sugar allyltin derivatives seemed to be a good solution to this problem [27]. Reaction of D-gluco-configurated allyltin 23 with aldehyde 24 provided the higher sugar skeleton 25 [28]. However, substantial amounts of product 26 resulting from decomposition of sugar allyltin 23 was formed (Scheme (6)). Optimization of the reaction conditions (catalyst, pressure) allowed to obtain the desired coupling product (of type 25) in good yield [29-31].
CH
SnBu
.C-H 1. BuLi
x^^PPh
GaK^C 21
O
y
Rib 22
,SnBu
23
BnO
26
(6)
The "unwanted" dienoaldehyde 26 was found to be very useful intermediate for the preparation of complex carbo-bicyclic derivatives which can be regarded as sugar mimetics.
III. Bicyclic sugar mimetics. The methodology of the preparation of bicyclic poly-hydroxylated derivatives exemplified by conversion of dienoaldehyde 26 into hydrindane or decalin skeleton was described in our review from 2008 [23].
Reaction of 26 with the Wittig-type reagent afforded triene 27 which underwent cy-clization (also under high pressure) to hydrindane 29 with trans ring junction (Scheme (7); route a). Alternatively it was converted to decalin 31 via intermediate phosphorane 28-I or phosphonate 28-II (route b) [23].
C(O)R
Wittig-type
COR
29 hydrindane
OBn
OBn
OO
31 decalin
OR OR
(7)
Examples of such polyhydroxylated derivatives prepared by us are shown in Scheme (8). The nitrogen containing bicyclic derivatives such as 33 or 34 are also available. Introduction
route a
of the nitrogen functionality at the C-1 position (for example via an oxime) allowed to prepare a wide variety of the nitrogen heterocycles such as 33 or 34 [32-35].
We have proposed also other useful routes to bicyclic sugar mimetics [36, 37], which currently are being pursued in our laboratory.
IV. The chemistry of sucrose. Sucrose (P-D-fructofuranosyl a-D-glucopyranoside), produced from sugar cane and sugar beet (in the scale > 150 mln tons per year) is the most available of all low molecular weight carbohydrates. Most of it is absorbed on the food market. However, since there is a big overproduction, many laboratories (especially industrial) use it as a renewable raw material [38-40].
Our developments in the field, exploration of which was strongly "suggested" to me by Prof. Makosza, was recently summarized in a review articles [41-43]. We elaborated a convenient route to 2, 3, 3', 4,4'-penta-0-benzyl- (38) and 1', 2, 3, 3', 4, 4-hexa-O-benzyl-sucrose (39) [44], based on the selective protection of either all primary hydroxyl groups (1'-OH, 6-OH, 6'-OH) or the most reactive ones (6-OH and 6'-OH). Subsequent protection of the remaining OH as benzyl ethers followed by removal of the trityl blocks afforded triol 38 and diol 39 (Scheme (9)).
OH
HO
H,,
HO HO
32
H
OH
OH
HO
33
OH
HQ OH
HO -, H
HO H
HO.'TvrH® ho "
HO
OH N
H
34
OH
glucose allyltin 23
AcO .OBn
HO HO
BnO
OBn OBn
35
HO OBn
R H OBn X = -P(O)Ph2 X = -SCN
OBn
OBn 36
(8)
OH
HO
a
HO HO
OH
1. Tri-tritylation at the C1', C6, C6' or di-tritylation at the C6,C6'
ru^^ 2. per-benzylation
OH 3. removal of trityl blocks
OH
HO
6'\
BnO <„, BnO
OBn
(9)
OH
OBn
OBn
37
38. R = H; 39. R = benzyl
Deprotection of the primary positions was the crucial step of both syntheses. Trityl blocks are usually removed under the acidic conditions, which usually induce also the hydrolysis of the glycosidic bond. Great care should be taken, therefore, in the preparation of 38 and 39.
Differentiation of all primary hydroxyl groups in 38 was possible (Scheme (10)). Its reaction with p-nitrobenzoic acid under the Mitsunobu conditions protected the most reactive hydroxyl groups at the C6- and C6'-positions and gave alcohol 40. Protection of the remaining 1'-OH either as MOM- or BOM-ether followed by basic hydrolysis afforded diol 41a or 41b. Treatment of the diol with either tert-butyldimethyl- or tert-butyldiphenyl-silyl chlorides was highly regioselective and afforded only one mono-protected derivative 42
in which the silyl block was installed at the "fructose end". Such selective silylation of free sucrose at the fructose "end" is known [45-47]. Reaction of diol 41 with an excess of silyl chloride gave the fully protected derivative 43; its selective deprotection at the 6'-position led to the last regioisomeric alcohol 44; this was our original finding [48].
OH
BnO
HO
\
OH
OH
OR
BnO
HO
<A
OBn^
OBn 38
41a. R = MOM 41b. R = BOM
selective mono-silylation
(10)
OSiROR
OH
a
5 x OBn^j 44
selective
de-silylation
(OSiRORR,SiO
5x_OBn>
OH
6
43
42
ORRSiO
a
5 x OBn
Such prepared alcohols were functionalized at either position affording the corresponding uronic acids, amines, or "homologated derivatives" with the untouched sucrose skeleton [49, 50].
We noted very interesting behavior of hexa-O-benzylsucrose (39) towards the ether forming reagents. Reaction of 39 with chloroacetonitrile protected the "glucose end" (C6) providing 45 [51], while the selective silylation protected the 6'-OH exclusively (46). The double silylated product 48 was selectively deprotected at the fructose "end" (47; see Scheme (11)) [52].
OSiR^SiO
^6 6'\
48
ch2cn
O
(11)
OH
a
45
OH R3SiO
6 3 a
6 x OBn
k
OSiR3
OH
46
Based on these observations we were able to install the phosphorus functionality (compounds 49-54) at either terminal position in hexa-O-benzylsucrose 39; (Scheme (12)) [52].
R' k.
R\
6'i
49. R' = R" = PPh2
50. R' = R'' = P(O)(OR)2
51. R' = OH; R" = PPh2
52. R' = PPh2; R'' = OH
53. R' = OH; R" = P(O)(OR)2
54. R' = P(O)(OR)2; R'' = OHI
V. Sucrose macrocyclic derivatives. The work presented in Chapter IV was the introduction to much more interesting area: the macrocyclic derivatives with sucrose scaffold. It is known that the terminal positions of both sub-units in free sucrose: glucose (C6) and fructose (C6') are close to each other in the most stable conformation in the solid state (55 in Scheme (13)) and also in solution [53]. This might suggest that the C6 and C6' positions could be connected via a linker.
Although we could not expect the same phenomenon, i. e. close vicinity of these terminal positions in protected sucroses (38, 39 or 41), the possible connection of them was challenging, since it might open a route to macrocyclic receptors with sucrose scaffold.
We have successfully realized this goal already in 2001. Connection of the 6, 6'-positions was achieved by a minimum four carbon atom unit as demonstrated by reaction of 41 with 1,4-di-iodobutane. We were able also to connect the terminal positions by RCM reaction of appropriately substituted sucroses; derivatives 56 and 57 were available (Scheme (14)) [54].
I-(CH2)4-I
NaH
OBn
41a. R = MOM, 39. R = Bn
1. All-Br vO 2. RCM
( MOMO \ "
P-O-^H
Cl
2. RCM
56
O
MOMO
i-
55
57
O
(14)
O
Connection of both terminal positions of sucrose was also possible by the RCM approach, for "unsymmetrical" derivative 59, prepared readily from 39. Cyclization, induced by the Grubbs II catalyst, afforded cyclic dimer 60 and several other products (including cyclic monomer and linear dimer) in low, however, yield (Scheme (15)) [55].
Another possibility of the connection of the terminal positions lays in click approach based on Huisgen reaction [56, 57]. Azidoacetylene 61, readily prepared from monosilylated hexa-O-benzylsucrose 46, underwent cyclization providing dimer 62 and the corresponding monomer (Scheme (16)) [58].
61
BnO, BnO"
O BnO
BnO
OBn
OBn
o-OBn
BnO O
rv-^ ..OBn N=N f ]
'■—O-^V^^Y^OBn
62 OBn
"click"
(16)
Another approach to symmetrical sucrose macrocyclic dimers from monosilylated derivative 46 is presented in Scheme (17). This unit (46) was connected with di-acetylene 63 (a or b) using a "click approach" to give dimer 64a, b. Cyclization of this product (to 65) was difficult. Activation of both fructose hydroxyls followed by reaction with ethanolodiamine could be realized only in the presence of phenylalanine as a template [59].
% #
46
kj v
tf
63a, b
BnO BnO d ^ BnO
N XN BnO 7
OBn
OH
_nh
O OH
N N BnO N
T^O
BnO-( У"O "OBn BnO W BnO
BnO BnO 64a, b
NH Cl-
+ nh3
P^--CO2Me
template
(17)
OBn 65a, b
Recently we proposed a route to other complex sucrose dimers such as 69. Compound 46 was converted to aldehyde 66 and separately to phosphonate 67. These two sub-units were coupled under the mild PTC conditions to afford enone 68 in good yield. Functionalization of the three-carbon unit connecting both sugars was troublesome, but finally stereoselective reduction of the carbonyl group (for the mechanism see Scheme (3)) and syn-dihydroxylation led to diol 69 (Scheme (18)) [60].
1. MsCl, Et3N
2. H2N
69
route b
68 OBn
(18)
VI. Synthesis of macrocyclic sucrose. Although the sucrose macrocycles presented in Chapter V are interesting, we turned our attention to the more "useful" derivatives such as crown ethers and their analogs. Such compounds play an important role in molecular recognition, being able to differentiate chiral guests and acting as chiral catalysts in enan-tioselective reactions [61-63].
Monosaccharides are convenient platforms for chiral macrocyclic receptors which are able to differentiate enantiomers [64, 65]. However, only limited examples of such receptors with di- or tri-saccharide scaffold are reported in the literature [64, 65].
In 2001 we have published the first paper describing the synthesis of sucrose-based crown ether analogs. Reaction of diol 39 or 41b (both having the 6- and 6'-hydroxyl groups unprotected) with polyethylene glycol ditosylates gave the corresponding macrocycles 70 in good (or moderate) yields. After total deprotection, these compounds were obtained in the free form (Scheme (19)) [66]. A variety of such crown ethers with sucrose scaffold were prepared [44].
Alternatively, diol 39 was converted into so-called homologated diol 71 by reaction with ieri-butyl bromoactete followed by reduction of both ester functions with LAH. Activation of the hydroxyl groups and subsequent reaction with benzylamine afforded aza-macrocycle 72 (Scheme (19)). Removal of the benzyl protections allowed to isolate the target compound as per-acetate; its structure was determined by X-ray [67].
Starting from diol 39 we were also able to prepare a wide variety of sucrose-based aza-coronands shown in Scheme (20) [68, 69].
Although these compounds had interesting complexing properties (see next chapter) they had also one disadvantage: the nitrogen atom(s) was always protected with the benzyl group which cannot be removed without deprotection of the whole skeleton of sucrose also protected with benzyl functions. It would be, however, advantageous to have this atom "free" which should allow to install different groups that might have an influence on the properties of the macrocycle. Starting from the selectively protected derivative 45, we were able to prepare aminoalcohol 80. Its cyclization was achieved with the Garegg's reagent (Ph3P/I2/imidazole) which converted the -CH2OH group into -CH2I; displacement of iodine with the nitrogen nucleophile provided macrocycle 81 (Scheme (21)). The hydrogen atom at the amine function could be replaced with various substituents [70].
39
(or)
41b
1. NaH/THF
2. Ts(OCH2CH2)n+iOTs
30-50 %
1. tbutylbromoacetate
2. LAH de-protected sucrose macrocycles
BnO.....
BnO
^"O'N/^OBn OBn OBn
\
n = 1 - 3 70a. R = BOM; 70b. R = Bn R
(19)
OH
O
O.
OH O
6'\
1. MsCl
2. Nal
3. BnNH
6 x OBn, 71
RO„ RO
- O bROR
OR OR 72. R = Bn; 73. R = Ac
NHBn BnHN
6' J
39
BnO BnO
Bn
Bn N N N Bn OBn
O 1\^>~OBn BnO.....
O
OH HO
NBn BnN
(6 6'\
I 76
BnN N Bn
OBn ) O O BnO ......O^^OBn
71
Bn
Bn
OBn
OBn
77
BnO
OBn
78
OBn
BnO
(20)
OBn
OBn
OBn
79
h2n
ch2cn
O2
OH
6'
OH
6 x OBn 45
2. LAH
O
80
H
r^O
OBn )
imidazole
BnO Bn
(21)
OBn
OBn 81
OBn
Other drawback in our standard synthesis of sucrose macrocycles was, that they were "symmetrical", i. e. the heteroatoms connected directly to the glucose and fructose parts (C6 and C6') were the same: either both oxygen or both nitrogen atoms.
Recently we have proposed the convenient way to "unsymmetrical" macrocycles with different heteroatoms at the terminal positions of sucrose. The idea is shown in Scheme (22).
Alcohol 46 with the 6-OH free was protected with tert-butyl bromoacetate, the 6'-OH was deprotected and oxidized to aldehyde 82 . Reductive amination of 82 with glycine derivative provided 83 which was reduced to aminoalcohol 84 . Cyclization of this derivative
1. BrCHCO'Bu
Ph3P/I2
promoted by the Garegg's reagent led to the first "unsymmetrical" macrocycle 85. The regioisomeric derivative 86 was prepared by the same method starting from alcohol 47 with the 6'-OH free [71].
(22)
OBn 86
We also succeeded in the preparation of another macrocycle — with the specifically blocked l'-position — from penta-O-benzyl sucrose 38. The 6- and 6'-"ends" were blocked and the l'-OH was protected as allyl ether; closing the ring between C6 and C6' provided macrocycle 87 (Scheme (23)) [72]. Potentially, the allyl functionality can be removed; this should open the route to macrocycles modified at the "internal" (i. e. Cl') position.
BnO BnO
oh
OH
O
BnO BnO 38
OH
OBn
1. protection of the 6-OH and 6'-OH
2. All-Br
3. closing of the ring between 6- and 6'
BnO BnO
^O U" OBn 87
(23)
OBn
OBn
It is known that macrocyclic lactams have interesting complexing properties. Isophthalic and pyridine-2,6-diamides are among the most common platforms used for the construction of such receptors [73]. Recently we proposed the synthesis of such bis-amides with sucrose scaffold. Reaction of 6'6'-di-O-mesyl hexa-O-methyl sucrose (88) with ortho- meta-and para-nitrophenols afforded di-ethers converted further into diamines 89. Treatment of them with proper di-acid chloride (90a, b) led to the corresponding cyclic di-amides 91 (Scheme (24)). In case of derivatives of p-nitrophenol, the yield of the final di-amide was low; the major product was a mixture of two regioisomeric dimers [74].
VII. Complexing properties of macrocyclic sucrose receptors. Our initial study on the complexation of simple achiral cations by our receptors showed that sucrose macrocycles containing the nitrogen atom in the ring form stronger complexes with simple ammonium cation than those containing only the oxygen atoms (1.7 • 101 for 70b and 1.25 • 102 for 72; Scheme (25)) [67, 68].
OMs
MeO MeO
O
OMe
O
MeO MeO 88
O
NH
/
NH
/ jj ortho-■ Ja meta-^O para- o'
6'\
6 x OBn ~91
MsO
OMe
1. nitrophenol
2. LAH
/NH2
O
O
90a. X = CH 90b. X = N
k
ortho-meta-O para- O
\ <A
6 x OBn 89
yields: 91 ortho: = 80 %; 91 meta: = 60 %; 91 para: = 30 % (+ dimers)
(24)
BnO.....
BnO
-O OBn
Bn
OBn OBn
OBn
BnO.,„^O BnO
OBn
(25)
OBn
OBn
70b. (n = 1). K(K+) = 2.5^102;
72. K(K+) = 2.5^102;
Ka(NH4+) = 17
K(NH4+) = 1.25^102
What about the receptors with more nitrogen atoms; what about enantioselectivity of complexation? This was studied in more detail for compounds 77-79.
Compound 77, with three protected nitrogen atoms in the ring, formed much stronger complex with ammonium cation than 72 [68]. What was more important, it was able to distinguish both enantiomers of the simplest chiral amine — a-phenylethylamine (92) — with low, however, enantioselectivity [69].
Larger sucrose receptors: 78 and 79 formed complexes only with the famine with moderate association constants (Scheme (26)) [69].
Position of the nitrogen atom in the ring (compounds 85 vs 86) had also the influence on the enantioselectivity of complexation. Presence of the nitrogen atom at the "glucose part" of the macrocycle decreases the enantioselectivity [71]. The substituent at the ring nitrogen had also significant influence on the complexing ability of the receptors as shown in Scheme (27) [70].
The best receptor 93c, was used for enantioselective complexation of aminoacids (in the form of the hydrochlorides of their methyl esters). The association constants were ca 103-104 in chloroform and ca 102 in DMSO. However the enantioselectivities (except for alanine) were low [70].
Bn
Bn—N NBn
¿OBn >
O
BnO
Bn
OBn OBn OBn 77
NH NH.
Ka(NH4+) = 5.6^102 k(S-92) = 1.2^103 K(R-92) = 8.4102 BnO"-
A' HCl „ ^
Ph ^ Ph ^ S-92 R-92
■ HCl
BnO
Bn
OBn
......io^o-v^"""
OBn
OBn
OBn
(26)
only complex with S-92 is formed
78. X = NBn; K = 5.6102
' a
79. X = O; K = 9.5102
N R
OBn
BnO
BnO
85. Ka(S-92) = 5.2-102 Kaa(R-92) not. det.
OBn 93a. R = Bn
OBn (27)
OBn K (S-92) K (R-92)
86. Ka(S-92) = 3.9102
Ka(R o2) = 1 3-i02 93b. R = pyridin-2-ylmethyl Ka(R-92) 1.3 10 93c. r = MeO-CH2CH2-
70
317
733
nd 67 nd
VIII. Conclusion. In this relatively short (although not very short) story I tried to present my scientific interest which was concentrated on sugar chemistry. Professor Mieczyslaw Makosza, the long-term Director of the Institute, had the strong influence on the direction of my research. In the beginning of my independent career, he did strongly "suggest" to switch my interest from higher carbon sugars to sucrose chemistry.
I must say that I was not happy at all to follow this "kind suggestion"! However, I feel now that pushing me to do something looking quite frustrating in the beginning, brought interesting results. The research on sucrose chemistry helped me to apply successfully for the project: "Sugars as raw materials for the preparation of compounds with high added value" co-financed (with very good money) by the European Union. This project, which I coordinate, is realized by a consortium of several chemical Polish institutions with the Institute of Organic Chemistry, PAS as a Leader.
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Статья поступила в редакцию 20 мая 2014 г.
Контактная информация
Jarosz Slawomir — Professor; e-mail: [email protected]
