Remote asymmetric induction:: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination

被引：29

作者：

Arya, P ^{[1
]}

Ben, RN ^{[1
]}

Qin, HP ^{[1
]}

机构：

[1] Natl Res Council Canada, Steacie Inst Mol Sci, Ottawa, ON K1A 0R6, Canada

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(98)01295-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A high diastereoselectivity (98%) for electrophilic amination of compound 9 using di-t-butyl azodicarboxyl ester as an electrophile was achieved. A similar reaction with compound 13 having achiral oxazolidinone was studied to examine 1,4-remote asymmetric induction. In the latter, a selectivity of 6.5:1 demonstrated the effect of alpha-galactosyl moiety, responsible for inducing the induction from the remote site. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6131 / 6134

页数：4

共 18 条

[1]

BEN RN, 1998, IN PRESS J ORG CHEM

[2] SYNTHESIS OF CARBON-LINKED GLYCOPEPTIDES AS STABLE GLYCOPEPTIDE MODELS [J].

BERTOZZI, CR ;

HOEPRICH, PD ;

BEDNARSKI, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6092-6094

[3] CARBON-LINKED GALACTOSPHINGOLIPID ANALOGS BIND SPECIFICALLY TO HIV-1 GP120 [J].

BERTOZZI, CR ;

COOK, DG ;

KOBERTZ, WR ;

GONZALEZSCARANO, F ;

BEDNARSKI, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10639-10641

[4] Chemical and biological approaches to glycoprotein synthesis [J].

Bill, RM ;

Flitsch, SL .

CHEMISTRY & BIOLOGY, 1996, 3 (03) :145-149

[5] Stereoselective synthesis of a C-glycosidic analog of N-glucoasparagine [J].

Burkhart, F ;

Hoffmann, M ;

Kessler, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11) :1191-1192

[6] Synthesis of carbon-linked glycopeptides through catalytic asymmetric hydrogenation [J].

Debenham, SD ;

Debenham, JS ;

Burk, MJ ;

Toone, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) :9897-9898

[7] Glycobiology: Toward understanding the function of sugars [J].

Dwek, RA .

CHEMICAL REVIEWS, 1996, 96 (02) :683-720

[8] STEREOSELECTIVE SYNTHESES OF RETRO-ISOMERS OF N-GLUCOASPARAGINE [J].

FREY, O ;

HOFFMANN, M ;

KESSLER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (18) :2026-2028

[9] SYNTHESIS OF (C)UNDER-BAR- ALPHA-D-GLUCOSYL-ALPHA-AMINO ACIDS [J].

GURJAR, MK ;

MAINKAR, AS ;

SYAMALA, M .

TETRAHEDRON-ASYMMETRY, 1993, 4 (11) :2343-2346

[10] SYNTHESIS OF C-GLYCOPEPTIDES VIA FREE-RADICAL ADDITION OF GLYCOSYL BROMIDES TO DEHYDROALANINE DERIVATIVES [J].

KESSLER, H ;

WITTMANN, V ;

KOCK, M ;

KOTTENHAHN, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (07) :902-904

← 1 2 →