N-Nosyl as a stereoselectivity-improving and easily removable group in the O-glycosylation of D-allal and D-galactal-derived allyl aziridines.: Stereospecific synthesis of 4-amino-2,3-unsaturated-O-glycosides

被引：14

作者：

Di Bussolo, Valeria ^{[1
]}

Romano, Maria Rosaria ^{[1
]}

Pineschi, Mauro ^{[1
]}

Crotti, Paolo ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

来源：

TETRAHEDRON | 2007年 / 63卷 / 11期

关键词：

allyl aziridines; glycals; glycosylation; amino sugars;

D O I：

10.1016/j.tet.2006.12.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The glycosylation of alcohols, phenol, and partially protected monosaccharides with the diastereoisorneric D-allal and D-galactal-derived N-nosyl aziridines 2 alpha and 2 beta leads to the corresponding 4-N-(nosylamino)-2,3 -unsaturated-alpha-O- (6 alpha) and beta-O-glycosides and disaccharides (6 beta), respectively, in a stereospecific substrate-dependent O-glycosylation process. The N-(nosylamino) group of 6 alpha and 6 beta can easily be deprotected to give the corresponding 4-amino-2,3-unsaturated-O-glycosides 7 alpha and 7 beta, with an increased value to our glycosylation protocol. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2482 / 2489

页数：8

共 2 条

[1] Stereoselective Synthesis of 4-Amino-2,3-unsaturated-N-Cbz-imino-O-glycosides via New Diastereoisomeric N-Cbz-Imino Glycal-Derived Allyl N-Nosyl Aziridines
Di Bussolo, Valeria
Fiasella, Annalisa
Favero, Lucilla
Bertolini, Ferruccio
Crotti, Paolo
ORGANIC LETTERS, 2009, 11 (12) : 2675 - 2678
[2] Stereoselective uncatalyzed synthesis of 2,3-unsaturated-4-N-substituted-β-O-glycosides by means of a new D-galactal-derived N-(mesyl)-aziridine
Di Bussolo, V
Romano, MR
Favero, L
Pineschi, M
Crotti, P
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04): : 1696 - 1699

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