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
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
收藏
页码:6131 / 6134
页数:4
相关论文
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