STEREOCONTROLLED SYNTHESIS OF AZIRIDINE-2-LACTONES FROM D-RIBOSE AND D-LYXOSE

被引：34

作者：

DUBOIS, L ^{[1
]}

DODD, RH ^{[1
]}

机构：

[1] INST CHIM SUBST NAT,CNRS,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON | 1993年 / 49卷 / 04期

关键词：

D O I：

10.1016/S0040-4020(01)80332-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (1S,4S,5R)-N-acetyl-4-methoxymethyl-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 15a, an optically pure, cyclic analogue of aziridine-2-carboxylates, is described starting from D-ribose. Key steps include triphenylphosphine-promoted conversion of a 3-azido-2-tosyl-D-xylofuranoside (10a) to its corresponding 2,3-aziridine 12a, selective cleavage of a 1-0-t-butyldimethylsilyl blocking group followed by TPAP oxidation of the anomeric hemiacetal group to the lactone 15a. The procedure is directly applicable to D-lyxose to give the enantiomerically pure (1R,4S,5S) isomer of 15a, 15b.

引用

页码：901 / 910

页数：10

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