Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine

被引：30

作者：

Cipolla, L

La Ferla, B

Lay, L

Peri, F

Nicotra, F

机构：

[1] Univ Milano Bicocca, Dipartimento Biotecnol & Biosci, I-20126 Milan, Italy

[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[3] CNR, Ctr Studio Sostanze Nat, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(99)00480-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Attempts to synthesise alpha-C-glycosides of N-acetylgalactosamine by selective deprotection at C-2' of allyl alpha-C-galactoside 1 and subsequent amination failed, but opened the way to alpha-C-talopyranosides. The synthesis of alpha-C-glycosides of N-acetylgalactosamine was performed from allyl alpha-C-glucopyranoside 9, which was regioselectively deprotected, stereoselectively aminated at C-2', and finally epimerised at C-4'. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：295 / 303

页数：9

共 28 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
AbdelMagid, AF
Carson, KG
Harris, BD
Maryanoff, CA
Shah, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
[2] Allinger NL, 1976, ORGANIC CHEM
[3] C-glycosides:: A stereoselective synthesis of α-C-galactosamines with a glycosyl dianion
Burkhart, F
Kessler, H
[J]. TETRAHEDRON LETTERS, 1998, 39 (3-4) : 255 - 256
[4] CARRAWAY K L, 1991, Glycobiology, V1, P131, DOI 10.1093/glycob/1.2.131
[5] New and easy access to C-glycosides of glucosamine and mannosamine
Cipolla, L
Lay, L
Nicotra, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) : 6678 - 6681
[6] Glycobiology: Toward understanding the function of sugars
Dwek, RA
[J]. CHEMICAL REVIEWS, 1996, 96 (02) : 683 - 720
[7] STEREOSELECTIVE SYNTHESIS OF ALPHA-C-ALLYL-GLYCOPYRANODISES
GIANNIS, A
SANDHOFF, K
[J]. TETRAHEDRON LETTERS, 1985, 26 (12) : 1479 - 1482
[8] SODIUM-BOROHYDRIDE IN CARBOXYLIC-ACID MEDIA - A REVIEW OF THE SYNTHETIC UTILITY OF ACYLOXYBOROHYDRIDES
GRIBBLE, GW
NUTAITIS, CF
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (4-5) : 317 - 384
[9] STEREOSELECTIVE SYNTHESIS OF 3-(D-GLYCOPYRANOSYL)PROPENES BY USE OF ALLYLSILANES
HOSOMI, A
SAKATA, Y
SAKURAI, H
[J]. CARBOHYDRATE RESEARCH, 1987, 171 : 223 - 232
[10] IPATKSCHI J, 1984, CHEM BER, V117, P856

← 1 2 3 →