Process for enantiomerically pure .beta.-L-1,3-oxathiolane nucle

Details Process for enantiomerically pure .beta.-L-1,3-oxathiolane nucle Process for enantiomerically pure .beta.-L-1,3-oxathiolane nucle

1991-12-05

1993-09-28

Tsang, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544182, 544180, 544265, 544264, 544276, 544277, 544298, 544313, 544315, 544317, C07D47332, C07D40504, A61K 31505

Patent

active

052487768

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).

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