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

被引：0
|
作者：
S. G. Polonik
V. A. Denisenko
机构：
[1] Far-Eastern Branch of the Russian Academy of Sciences,Pacific Institute of Bioorganic Chemistry
来源：
Russian Chemical Bulletin | 2009年 / 58卷
关键词：
1,4-naphthoquinones; thioglycosides; heterocyclization; tetracyclic compounds; condensed sugars; naphtho[2,3-; ]pyrano[2,3-; ][1,4]oxathiines;
D O I：
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中图分类号：
学科分类号：
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.
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页码：1062 / 1066
页数：4
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