A ONE-POT SYNTHESIS OF DIMETHYL 2,3-O-BENZYLIDENE-L-TARTRATE FROM L-TARTARIC ACID

被引：6

作者：

BYUN, HS ^{[1
]}

BITTMAN, R ^{[1
]}

机构：

[1] CUNY QUEENS COLL,DEPT CHEM & BIOCHEM,FLUSHING,NY 11367

来源：

SYNTHETIC COMMUNICATIONS | 1993年 / 23卷 / 22期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1080/00397919308011180

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An economical one-pot synthesis of (-)-dimethyl 2,3-O-benzylidene-L-tartrate [(4R,5S)-4,5-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolane] and its enantiomer from the corresponding tartaric acids is reported in 83-91% yield. The desired benzylidene tartrate is obtained by reaction of tartaric acid and benzaldehyde (1.5 equiv) in the presence of p-toluenesulfonic acid in methanol followed by the addition of 3 equiv of trimethyl orthoformate, which reacts with the water generated in the reaction.

引用

页码：3201 / 3204

页数：4

共 7 条

[1]

ALHAKIM AH, 1985, SYNTHESIS-STUTTGART, P207

[2]

BUCKLES RE, 1963, ORG SYNTH, V4, P778

[3] AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF PLATELET-ACTIVATING FACTORS AND THE ENANTIOMERS FROM D-TARTARIC AND L-TARTARIC ACIDS [J].