Process for the preparation of trans-3-alkyloxy-4-hydroxytetrahy

Details Process for the preparation of trans-3-alkyloxy-4-hydroxytetrahy Process for the preparation of trans-3-alkyloxy-4-hydroxytetrahy

1999-12-15

2000-10-31

Dentz, Bernard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549478, 435126, C07D30910, C12P 1704

Patent

active

061405167

ABSTRACT:
Disclosed is a process for preparing novel trans-3-alkyloxy-4-hydroxytetrahydrofurans including racemic and substantially enantiomerically pure (3S,4S)-trans-3-alk(en)yloxy-4-hydroxytetrahydrofurans and (3R,4R)-trans-3-alk(en)yloxy-4-acyloxytetrahydrofurans. The disclosed process comprises the steps of reacting 3,4-epoxytetrahydrofuran with an alcohol under Lewis acid catalysis to obtain a racemic trans-3-alk(en)yloxy-4-hydroxytetrahydrofuran; contacting the trans-3-alk(en)yloxy-4-hydroxytetrahydrofuran with an acyl donor in the presence of a hydrolase enzyme to produce a mixture of a substantially enantiomerically pure (3S,4S)-trans-3-alk(en)yloxy-4-hydroxytetrahydrofuran and a substantially enantiomerically pure (3R,4R)-trans-3-alk(en)yloxy-4-acyloxytetrahydrofuran; and separating the components of the mixture by partitioning between water and a solvent immiscible with water.

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