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Synthesis and p-diastereomeric resolution of nucleoside 3′-O(s-alkyl) and nucleoside 3′-O(s-aryl) methylphosphonothioates

✍ Scribed by Wolfgang K.-D. Brill; Marvin H. Caruthers

Book ID: 104216464
Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 323 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)80262-2

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✦ Synopsis

Successive displacement of oxybenzotriszoyl moieties from methylphosphonicbisoxybenzotriazolide by a deoxynucleoside and a mercaptan yields the O,S-dialkyl and O-alkyl-S-arylmethylphosphonothioate diastereomers which can be resolved by flash column chromatography.

Nucleotide analogs bearing a chiral phosphate are of potential significance for many enzymological and medicinal uses. 1 Alkylphosphonothioate analogs appear attractive to us for these applications because they are chiral and do not racemize easily in aqueous solutions.

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