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[与阿昔洛韦类似的化合物。VI. 光学活性1',2'-链核苷的合成]

[Compounds similar to acyclovir. VI. Synthesis of optically active 1',2'-seconucleosides].

作者信息

Smirnov I P, Kochetkova S V, Tsilevich T L, Khorlin A A, Gottikh B P, Florent'ev V L

出版信息

Bioorg Khim. 1990 Oct;16(10):1355-61.

PMID:2085327
Abstract

A convenient method is suggested of synthesis of (3R, 4R)-, (3S, 4S)- and (3R/S, 4S/R)-dihydroxy-3-hydroxymethyl-2-oxapentyl derivatives of the, cytosine, uracyl, adenine and guanine ("full" acyclic analogues of nucleosides with C1'-C2' bond cleaved) by condensation of trimethylsilyl derivatives of nucleic bases (sodium salt in case of adenine) with (3$, 4R)-, (3S )-, (3S, 4S)- and (3R/S, 4S/R)-4,5-diacetoxy-3-acetoxymethyl-1-chloro-2-oxapentanes without catalyst followed by deacetylation.

摘要

有人提出了一种简便的方法，通过核酸碱基的三甲基硅烷基衍生物（腺嘌呤的钠盐）与(3$, 4R)-、(3S )-、(3S, 4S)-和(3R/S, 4S/R)-4,5-二乙酰氧基-3-乙酰氧基甲基-1-氯-2-氧杂戊烷在无催化剂的情况下缩合，然后进行脱乙酰化反应，来合成胞嘧啶、尿嘧啶、腺嘌呤和鸟嘌呤的(3R, 4R)-、(3S, 4S)-和(3R/S, 4S/R)-二羟基-3-羟甲基-2-氧杂戊基衍生物（具有C1'-C2'键断裂的核苷的“全”无环类似物）。

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