Chemical modification of the sugar moiety of pyrimidine nucleosides via a 4 ',5 '-epoxyuridine intermediate

The reaction of 4',5'-unsaturated nucleoside (5) with m-CPBA provided different products depending on the solvent. 4',5'-Epoxynucleoside (6) was generated as a key intermediate although 6 was not stable enough to isolate and further reaction progressed. When the reaction was perf...

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Bibliographic Details
Published inHeterocycles Vol. 65; no. 12; pp. 2991 - 2999
Main Authors Takasu, H, Sajiki, H, Hirota, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.12.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
4',5'-unsaturated uridine
URIDINE
4'5'-epoxyuridine
4'-alkoxyuridine
modification
m-CPBA
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Summary:The reaction of 4',5'-unsaturated nucleoside (5) with m-CPBA provided different products depending on the solvent. 4',5'-Epoxynucleoside (6) was generated as a key intermediate although 6 was not stable enough to isolate and further reaction progressed. When the reaction was performed in CH2Cl2, 2,4'-cyclonucleoside (7) and 4'-ketonucleoside (8) were obtained. On the other hand, 4'-alkoxy derivatives (9 and 11) together with their epimers (10 and 12) were aquired as a mixture by the nucleophilic attack of alcohol.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-05-10551