Synthesis of α- and β-C-glycosides of N-acetylglucosamine

被引：21

作者：

McGarvey, GJ ^{[1
]}

Schmidtmann, FW ^{[1
]}

Benedum, TE ^{[1
]}

Kizer, DE ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22903 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 19期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(03)00818-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3775 / 3779

页数：5

共 42 条

[1] Asensio JL, 2000, CHEM-EUR J, V6, P1035, DOI 10.1002/(SICI)1521-3765(20000317)6:6<1035::AID-CHEM1035>3.0.CO
[2] 2-G
[3] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES
BAL, BS
CHILDERS, WE
PINNICK, HW
[J]. TETRAHEDRON, 1981, 37 (11) : 2091 - 2096
[4] THE SYNTHESIS OF 2-AZIDO C-GLYCOSYL SUGARS
BERTOZZI, CR
BEDNARSKI, MD
[J]. TETRAHEDRON LETTERS, 1992, 33 (22) : 3109 - 3112
[5] Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine
Cipolla, L
La Ferla, B
Lay, L
Peri, F
Nicotra, F
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (01) : 295 - 303
[6] Stereocontrolled allylation of 2-amino-2-deoxy sugar derivatives by a free-radical procedure
Cui, JR
Horton, D
[J]. CARBOHYDRATE RESEARCH, 1998, 309 (04) : 319 - 330
[7] Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides
Dondoni, A
Marra, A
[J]. CHEMICAL REVIEWS, 2000, 100 (12) : 4395 - +
[8] Recent advances in stereoselective C-glycoside synthesis
Du, YG
Linhardt, RJ
Vlahov, IR
[J]. TETRAHEDRON, 1998, 54 (34) : 9913 - 9959
[9] Glycobiology: Toward understanding the function of sugars
Dwek, RA
[J]. CHEMICAL REVIEWS, 1996, 96 (02) : 683 - 720
[10] Escherichia coli β-galactosidase recognizes a high-energy conformation of C-lactose, a nonhydrolizable substrate analogue.: NMR and modeling studies of the molecular complex
Espinosa, JF
Montero, E
Vian, A
García, JL
Dietrich, H
Schmidt, RR
Martín-Lomas, M
Imberty, A
Cañada, FJ
Jiménez-Barbero, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (06) : 1309 - 1318

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