NUCLEOSIDES AND NUCLEOTIDES .134. SYNTHESIS OF 2'-C-ALKYNYL-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLPYRIMIDINES VIA RADICAL DEOXYGENATION OF TERT-PROPARGYL ALCOHOLS IN THE SUGAR MOIETY

被引：19

作者：

IINO, T ^{[1
]}

YOSHIMURA, Y ^{[1
]}

MATSUDA, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA KU,SAPPORO 060,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 35期

关键词：

NUCLEOSIDE; RADICAL DEOXYGENATION; BRANCHED-CHAIN SUGAR NUCLEOSIDE; ALKYNE; RADICAL REACTION; CYTOTOXICITY;

D O I：

10.1016/S0040-4020(01)89580-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 2'-deoxy-2'-C-ethynyl-1-beta-D-arabinofuranosyluracil (8c),-thymine (8f), and -cytosine (11) has been done by sterospecific radical deoxygenation of the corresponding 2'-tert-TMSpropargyl methoxalyl esters with Bu3SnH in the presence of AIBN. 2'-Deoxy-2'-C-hexynyl derivative 8d was also prepared under similar conditions. On the other hand, the deoxygenation of the phenylpropargyl or progargyl esters gave complex mixtures due to hydrostannylation of the triple bonds.

引用

页码：10397 / 10406

页数：10

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