Nitrogen inversion as a diastereomeric relay in azasugar synthesis: The first synthesis of adenophorine

被引：55

作者：

Maughan, MAT

Davies, IG

Claridge, TDW

Courtney, S

Hay, P

Davis, BG

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Univ Durham, Dept Chem, Durham DH1 3LE, England

[3] Oxford Glycosci Ltd, Abingdon OX14 4RY, Oxon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 32期

基金：

英国生物技术与生命科学研究理事会;

关键词：

asymmetric synthesis; azasugars; carbohydrates; glycosidase inhibitors; imines; stereodynamics;

D O I：

10.1002/anie.200351002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A temperature-dependent relay of chirality is based on the inversion of the nitrogen lone pair in cyclic azasugars. Elimination from the conformation preferred at a given temperature leads to a cyclic imine, and in a subsequent nucleophilic attack the stereochemical information is relayed.

引用

收藏

页码：3788 / 3792

页数：5

相关论文

共 56 条

[1]

ANET FAL, 1977, TETRAHEDRON LETT, V18, P3207

[2] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[3] STEREOCHEMISTRY OF THE CONVERSION OF 1,3-CHLOROALCOHOLS IN ALKALINE-MEDIUM - THE CHEMISTRY OF 1,3-BIFUNCTIONAL SYSTEMS .22. [J].

BARTOK, M ;

FELFOLDI, K ;

BOZOKIBARTOK, G .

HELVETICA CHIMICA ACTA, 1980, 63 (08) :2173-2178

[4] The first example of a 6-C-aryl-D-glucose: Inhibition of glucokinase [J].

Bleriot, Y ;

Veighey, CR ;

Smelt, KH ;

Cadefau, J ;

Stalmans, W ;

Biggadike, K ;

Lane, AL ;

Muller, M ;

Watkin, DJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2761-2772

[5] SECRETION OF HUMAN HEPATITIS-B VIRUS IS INHIBITED BY THE IMINO SUGAR N-BUTYLDEOXYNOJIRIMYCIN [J].

BLOCK, TM ;

LU, XY ;

PLATT, FM ;

FOSTER, GR ;

GERLICH, WH ;

BLUMBERG, BS ;

DWEK, RA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (06) :2235-2239

[6] REACTION OF 1-IODO-2-(PERFLUOROALKYL) CYCLOHEXANE CONFORMERS - PRODUCTS OF ELIMINATION + REDUCTION - RATES + MECHANISMS [J].

BRACE, NO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (12) :2428-&

[7]

BRUCE NO, 1964, J AM CHEM SOC, V86, P2428

[8] Chiral relay auxiliaries [J].

Bull, SD ;

Davies, SG ;

Fox, DJ ;

Garner, AC ;

Sellers, TGR .

PURE AND APPLIED CHEMISTRY, 1998, 70 (08) :1501-1506

[9] Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis [J].

Butters, TD ;

van den Broek, LAGM ;

Fleet, GWJ ;

Krulle, TM ;

Wormald, MR ;

Dwek, RA ;

Platt, FM .

TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :113-124

[10] Inhibition of glycosphingolipid biosynthesis: Application to lysosomal storage disorders [J].

Butters, TD ;

Dwek, RA ;

Platt, FM .

CHEMICAL REVIEWS, 2000, 100 (12) :4683-+

← 1 2 3 4 5 6 →