A NEW SYNTHESIS OF L-ASCORBIC-ACID FROM D-GALACTOSE

被引：13

作者：

BARILI, PL ^{[1
]}

BERTI, G ^{[1
]}

DANDREA, F ^{[1
]}

DIBUSSOLO, V ^{[1
]}

GRANUCCI, I ^{[1
]}

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY

来源：

TETRAHEDRON | 1992年 / 48卷 / 30期

关键词：

2,6-ANHYDRO-3-DEOXY-HEX-2-ENONIC ACIDS; HEX-2-ULOPYRANOSONATES; ELIMINATIONS; CONFORMATIONS;

D O I：

10.1016/S0040-4020(01)88219-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1.5-Anhydro-D-galactitol, easily available from D-galactose, was selectively protected in positions 2, 3 and 4 and converted into 5-O-acetyl-2,6-anhydro-3-deoxy-L-threo-hex-2-enonic acid methyl ester, which, on reaction with MCPBA in acetic acid gave 2.5-di-O-acetyl-alpha-L-lyxo-hex-2-ulopyranosonic acid methyl ester. Reaction of the latter with sodium methoxide produced sodium L-ascorbate in high yield. Several side-reactions and the conformations of some of the intermediates are also discussed.

引用

页码：6273 / 6284

页数：12

共 22 条

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