How to convert enantiomers - (2R, 3R) (2S, 3S) -2-amino-3-phenyl-1,3-propanediol

摘要

PURPOSE: To obtain (2R,3R)enantiomers effectively used in the synthesis of a compound having an antibiotic action, by successively carrying out the epimerization of only 2-position carbon atom combined with an amino group of a titled compound, and the epimerization of only 3-position benzyl carbon. ;CONSTITUTION: The OH group and NH₂ group at the 3-position of (2S,3S) enantiomer of a compound of formula (X is H, NO₂, CH₃S, CH₃SO, CH₃SO₂) are protected, then the hydroxymethyl group is oxidized to formyl or formyl derivative, carboxyl or carboxyl derivative by Swan-Moffatt oxidation, etc., and then a C atom at the α-position relative to the oxidized group is epimerized under an acid or base condition. The oxidized group of the obtained compound is reduced with a neutral reducing agent to be restored to the primary alcohol, the protective group introduced in the first process, is removed, and the benzyl carbon of 3-position is epimerized with acetic anhydride and p-toluenesulfonic anhydride, to obtain (2R,3R)enantiomer.;COPYRIGHT: (C)1991,JPO