ADDITIONAL REACTIONS OF SUGAR OXIMES, NITRILE OXIDES AND HYDROXIMOLACTONES

被引：27

作者：

YOKOYAMA, M

SUJINO, K

IRIE, M

YAMAZAKI, N

HIYAMA, T

YAMADA, N

TOGO, H

机构：

[1] Department of Chemistry, Faculty of Science, Chiba University, Chiba City 260, Yayoi-cho

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 11期

关键词：

D O I：

10.1039/p19910002801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of sugar oximes with dimethyl acetylenedicarboxylate gave chiral isoxazolines bearing a sugar moiety. Sugar nitrile oxides reacted with 1,3-dipolarophiles to afford the corresponding isoxazoles bearing a sugar moiety. Sugar hydroximolactones underwent a tandem Michael addition-1,3-dipolar cycloaddition by reaction with Michael acceptors to give the corresponding spiro sugar isoxazolidines. An X-ray crystallographic structure determination of (3S,5R,7R,8R,9R)-3-acetyl-8,9-isopropylidenedioxy-1-(3-oxobutyl)-7-trityloxymethyl-2,6-dioxa-1-azaspiro[4.4]nonane has been performed.

引用

页码：2801 / 2809

页数：9

共 21 条

[1] OXIDATION OF ALDOSE OXIMES - FORMATION AND STRUCTURE OF HYDROXYDIAZENE OXIDE ACETALS AND PREPARATION OF HYDROXIMOLACTONES - X-RAY CRYSTAL-STRUCTURE OF 2,3-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSYL-ONN-AZOXY 2,3-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE [J].