Journal of Organic Chemistry 2004-08-06

Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.

Xuequan Lu, Hoe-Sup Byun, Robert Bittman

Index: J. Org. Chem. 69(16) , 5433-8, (2004)

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Abstract

The first synthesis of an isosteric phosphonate analogue of the aminotriol lipid phytosphingosine (3), together with an improved synthesis of (2S,3S,4S)-phytosphingosine (2), are described. A key intermediate is 3-pentylidene acetal 9, which was prepared in two steps from dimethyl 2,3-O-benzylidene-d-tartrate (7).Copyright 2004 American Chemical Society