REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF CARBOHYDRATE ISOXAZOLIDINES BY 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO 5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-HEX-5-ENOFURANOSE

被引：12

作者：

ALTIMARI, UAR

FISERA, L

GOLJER, I

ERTL, P

机构：

[1] SLOVAK UNIV TECHNOL BRATISLAVA, DEPT ORGAN CHEM, CS-81237 BRATISLAVA, SLOVAKIA

[2] SLOVAK UNIV TECHNOL BRATISLAVA, CENT LAB CHEM TECH, CS-81237 BRATISLAVA, SLOVAKIA

[3] COMENIUS UNIV BRATISLAVA, INST CHEM, CS-84215 BRATISLAVA, SLOVAKIA

来源：

CARBOHYDRATE RESEARCH | 1992年 / 226卷 / 01期

关键词：

D O I：

10.1016/0008-6215(92)84054-V

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of 2-phenyl-3-aryl and 2-phenyl-3-aroyl derivatives 5-(1,2-O-isopropylidene-alpha-D-xylo-tetrofuranos-4-yl) isoxazolidine (3) from nitrones and 5,6-dideoxy-1,2-O-isopropylidene-alpha-D-xylo-hex-5-enofuranose (1) is described. The 1,3-dipolar cycloaddition reactions give mainly anti adducts 3 and 4 (greater-than-or-equal-to 95% pi-facial stereoselectivity). The cycloadducts 3 with H-3,5 cis are formed either exclusively or preponderate over the trans diastereoisomers 4.

引用

页码：49 / 56

页数：8

共 28 条

[1]

ALTIMARI UAR, 1991, CARBOHYD RES, V218, P121

[2]

ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253

[3] THE DIASTEREOSELECTIVITY OF INTERMOLECULAR NITRONE CYCLOADDITION TO CHIRAL ALLYL DERIVATIVES [J].