Synthesis and properties of fused tetracyclic derivatives of 1,4-naphthoquinone thioglycosides

被引：6
|
作者：
Polonik, S. G. [1 ]
Denisenko, V. A. [1 ]
机构：
[1] Russian Acad Sci, Pacific Inst Bioorgan Chem, Far Eastern Branch, Vladivostok 690022, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2009年 / 58卷 / 05期
关键词：
1,4-naphthoquinones; thioglycosides; heterocyclization; tetracyclic compounds; condensed sugars; naphtho[2,3-b]pyrano[2,3-e][1,4]oxathiines;
D O I：
10.1007/s11172-009-0135-y
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A series of 1,4-naphthoquinone O-acetylthioglycosides have been synthesized by the condensation of fully O-acetylated derivatives of 1-thio-d-xylose, 1-thio-L-arabinose, 1-thio-d-galactose, 1-thio-d-mannose, and 1-thiomaltose with 3-chloro-2-methoxy-1,4-naphtho-quinone. Their deacetylation with MeONa/MeOH proceeded with simultaneous heterocyclization to yield linear carbohydrate-containing tetracyclic quinones. Tetracycles with trans junction of the carbohydrate and quinone rings are poorly soluble in water and organic solvents.
引用
收藏
页码：1062 / 1066
页数：5
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