SYNTHESIS OF PER-O-ALKYLATED 5-THIO-D-GLUCONO-1,5-LACTONES AND TRANSANNULAR PARTICIPATION OF THE RING SULFUR ATOM OF 5-THIO-D-GLUCOSE DERIVATIVES ON SOLVOLYSIS UNDER ACIDIC CONDITIONS

被引：37

作者：

YUASA, H ^{[1
]}

TAMURA, J ^{[1
]}

HASHIMOTO, H ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,FAC SCI,DEPT LIFE SCI,MIDORI KU,YOKOHAMA,KANAGAWA 227,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 10期

关键词：

D O I：

10.1039/p19900002763

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Per-O-alkylated 5-thio-D-glucono-1,5-lactones (33)-(35) were synthesized via acetolysis or hydrolysis of the corresponding methyl glycosides (21)-(23). Transannular participation of the sulphur atom on acid methanolysis of 3,6-di-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-5-thio-α-D-glucofuranose and on acetolysis of the glycosides (21)-(23) was confirmed. These reactions gave unexpected 4-substituted derivatives (14), (28) and (29). Furthermore, similar participation on C-2 and C-6 was suggested from the formation of 2,5-dideoxy-2,5-epithio-4,6-di-O-methyl-D-mannose dimethyl acetal.

引用

页码：2763 / 2769

页数：7

共 22 条

[1]

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