Efficient Synthesis of Gemcitabine 5′-O-Triphosphate Using Gemcitabine 5′-O-Phosphoramidate as an Intermediate

被引：3

作者：

Kaczmarek, Renata ^{[1
]}

Radzikowska, Ewa ^{[1
]}

Baraniak, Janina ^{[1
,2
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Bioorgan Chem, PL-90363 Lodz, Poland

[2] Jan Dlugosz Univ, Inst Chem Environm Protect & Biotechnol, PL-42201 Czestochowa, Poland

来源：

SYNLETT | 2014年 / 25卷 / 13期

关键词：

oxathiaphosphorylation; gemcitabine 5 '-O-phosphate; gemcitabine 5 '-O-phosphoramidate; gemcitabine 5 '-O-triphosphate; OXATHIAPHOSPHOLANE APPROACH; TRIPHOSPHATE; PHOSPHOROTHIOYLATION; POLYOLS; ANALOGS;

D O I：

10.1055/s-0034-1378353

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient approach for the synthesis of gemcitabine triphosphate has been developed. The method is based on the ring-opening reaction of 2-cyanoethoxy-2-oxo-1,3,2-oxathiaphospholane with protected gemcitabine in the presence of DBU. Subsequent treatment of gemcitabine monophosphate with DCC in the presence of ammonia provides gemcitabine 5'-O-phosphoramidate. Finally, this compound, on reaction with pyrophosphate, furnishes gemcitabine 5'-triphosphate in 50% yield.

引用

页码：1851 / 1854

页数：4

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