有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
鎖状の立体化学を制御したチオ糖類の合成とチオ糖を糖部とする擬似ヌクレオシド合成
上西 潤一
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1997 年 55 巻 3 号 p. 186-195

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Chemical modification of the sugar moiety in nucleoside is one of the promising way to find a new chemotherapeutic agent. Nucleoside possessing a heterocyclic or carbocyclic ring instead of 2-deoxyribose or ribose is so called pseudo nucleoside. Since HIV (human immunodeficiency virus) has appeared to cause the serious disease in the human life, such nucleosides have received considerable attentions as a new anti-viral medicine. 4' -Thio-nucleoside in which furanose ring oxygen atom is replaced by a sulfur atom, is of our interest and this review describes the synthesis of 2' -deoxy-4' -thioribonucleo-sides. Specific features in this article include (i) preparation of 2-mercapto-1, 3-diols by acyclic stereocontrol, (ii) synthesis of 2-deoxy-4-thioribose, (iii) glycosidation reaction of thiosugar, and (iv) synthesis and biological activity of 2' -deoxy-4' -thio pyrimidine nucleosides.

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