Alternative Synthesis of 2'-Deoxy-6, 2'-methano-pyrimidine Nucleosides : Nucleosides and Nucleotides. XC

An alternative method for the synthesis of 2'-deoxy-6, 2'-methanouridine (1), -cytidine (3) and -4-thiouridine (13) is described which involves a condensation of an isopropyl β-D-2-pentuloside (5) and a carbanion formed from 6-trimethylsilylmethylpyrimidine (6), followed by intramolecular...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 38; no. 2; pp. 389 - 392
Main Authors YOSHIMURA, Yuichi, MATSUDA, Akira, UEDA, Tohru
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 25.02.1990
公益社団法人日本薬学会
Subjects
2'-deoxy-6, 2'-methano-4-thiouridine
2'-deoxy-6, 2'-methanocytidine
2'-deoxy-6, 2'-methanouridine
carbon-bridged cyclonucleoside
intramolecular glycosylation
ketosugar
nucleoside conformation
Peterson olefination
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ISSN0009-2363
1347-5223
DOI10.1248/cpb.38.389

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Summary:An alternative method for the synthesis of 2'-deoxy-6, 2'-methanouridine (1), -cytidine (3) and -4-thiouridine (13) is described which involves a condensation of an isopropyl β-D-2-pentuloside (5) and a carbanion formed from 6-trimethylsilylmethylpyrimidine (6), followed by intramolecular glycosylation.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.38.389