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

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...

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Bibliographic Details
Published inSynlett Vol. 25; no. 13; pp. 1851 - 1854
Main Authors Kaczmarek, Renata, Radzikowska, Ewa, Baraniak, Janina
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
POLYOLS
OXATHIAPHOSPHOLANE APPROACH
gemcitabine 5 '-O-phosphate
gemcitabine 5 '-O-phosphoramidate
PHOSPHOROTHIOYLATION
ANALOGS
oxathiaphosphorylation
gemcitabine 5 '-O-triphosphate
TRIPHOSPHATE
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1378353