DIOXOLANE NUCLEOSIDES AND THEIR PHOSPHONATE DERIVATIVES - SYNTHESIS AND HYDROLYTIC STABILITY

被引：7

作者：

EFIMTSEVA, EV

MIKHAILOV, SN

MESHKOV, S

HANKAMAKI, T

OIVANEN, M

LONNBERG, H

机构：

[1] UNIV TURKU,DEPT CHEM,SF-20500 TURKU,FINLAND

[2] RUSSIAN ACAD SCI,VA ENGELHARDT MOLEC BIOL INST,MOSCOW 117984,RUSSIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 11期

关键词：

D O I：

10.1039/p19950001409

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several new nucleoside (12-15):and nucleoside phosphonate (27-30) analogues derived from (+/-)-cis-and -trans-2-hydroxymethyl-4-methyl-1,3-dioxolane have been prepared and their configurations assigned by H-1 NMR spectroscopy. First-order rate constants for the acid-catalysed hydrolysis of the dioxolane ring have been determined at different hydronium ion concentrations. The phosphonate group accelerates the hydrolysis at pH > 2 by 2 orders of magnitude, while at pH < 1 the hydrolytic stabilities of the nucleoside analogues and their phosphonate derivatives are comparable. The possible reasons for this rate-enhancement are discussed on the basis of the reaction mechanism.

引用

页码：1409 / 1415

页数：7

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