Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides

被引：24

作者：

Bianchi, A ^{[1
]}

Bernardi, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 10期

关键词：

carbohydrates; glycosyl amides; ligation reactions; stereoselective synthesis;

D O I：

10.1016/j.tetlet.2003.12.159

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Glycosyl azides can be transformed into the corresponding alpha-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The of alpha-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2231 / 2234

页数：4

共 15 条

[1] Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines
Boullanger, P
Maunier, V
Lafont, D
[J]. CARBOHYDRATE RESEARCH, 2000, 324 (02) : 97 - 106
[2] AN EASILY INTRODUCED AND REMOVED PROTECTING GROUP FOR IMIDAZOLE NITROGEN - A CONVENIENT ROUTE TO 2-SUBSTITUTED IMIDAZOLES
CURTIS, NJ
BROWN, RS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) : 4038 - 4040
[3] Stereoselective synthesis of α- and β-glycosylamide derivatives from glycopyranosyl azides via isoxazoline intermediates
Damkaci, F
DeShong, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) : 4408 - 4409
[4] Mechanistic studies on the stereoselective formation of glycosyl iodides: First characterization of beta-D-glycosyl iodides
Gervay, J
Nguyen, TN
Hadd, MJ
[J]. CARBOHYDRATE RESEARCH, 1997, 300 (02) : 119 - 125
[5] SYNTHESIS, STRUCTURE AND REACTIONS OF GLYCOSYL AZIDES
GYORGYDEAK, Z
SZILAGYI, L
PAULSEN, H
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (02) : 139 - 163
[6] Glycosyl iodides are highly efficient donors under neutral conditions
Hadd, MJ
Gervay, J
[J]. CARBOHYDRATE RESEARCH, 1999, 320 (1-2) : 61 - 69
[7] An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides
Kovács, L
Osz, E
Domokos, V
Holzer, W
Györgydeák, Z
[J]. TETRAHEDRON, 2001, 57 (21) : 4609 - 4621
[8] Mizuno M, 1999, SYNTHESIS-STUTTGART, P162
[9] A versatile, three-component-reaction route to N-glycosylamines
Nair, LG
Fraser-Reid, B
Szardenings, AK
[J]. ORGANIC LETTERS, 2001, 3 (03) : 317 - 319
[10] Staudinger ligation: A peptide from a thioester and azide
Nilsson, BL
Kiessling, LL
Raines, RT
[J]. ORGANIC LETTERS, 2000, 2 (13) : 1939 - 1941

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