Process for enantiomerically pure .beta.-L-1,3-oxathiolane nucleosides
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorsChung K. Chu, Lak-Shin Jeong, J. Warren Beach
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Abstract
An asymmetric process for the preparation of enantiomerically pure .beta.-L-(-)-1,3-oxathiolane-nucleosides that includes the initial preparation of the key chiral intermediates (2R,5R) and (2R,5S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane from 1,6-thioanhydro-L-gulose. The 2R,5(R,S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane is condensed with a desired heterocyclic base, typically a purine or pyrimidine base, to provide the product nucleoside. The synthesis can be used to prepare the pharmaceutically important compound, .beta.-L-(-)-1-[(2.beta.,4.beta.)-2-(hydroxymethyl)-4-(1,3-thioxolane)]cyt osine (.beta.-L-(-)BCH-189).
Claims10
A process for the preparation of enantiomerically pure .beta.-L-(-)-1,3-oxathiolane nucleosides comprising preparing the 1,3-oxathiolane ring from 1,6-dideoxy-1,6-thioanhydro-L-gulose.
Dependencies are inferred from the claim text.