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A convenient method for the conversion of β-thymidine to α-thymidine based on TMSOTf-mediated C1′-epimerization

✍ Scribed by Yuichi Sato; Gohsuke Tateno; Kohji Seio; Mitsuo Sekine

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 66 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00411-2

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✦ Synopsis

A practically useful method for the synthesis of a-thymidine from b-thymidine was developed by trimethylsilyl triflate-mediated C1%-epimerization. When 5%-O-diphenylacetyl-3%-O-toluoylthymidine was trimethylsilylated and successively treated with TMSOTf in acetonitrile, the resulting a-thymidine derivative was crystallized and isolated without silica-gel column chromatography. Deprotection gave unprotected a-thymidine in an overall yield of 50% from b-thymidine.

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