Synthetic studies on sphingolipids. Part 5. Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides

D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl-D-glu cosamine 3 by an improved route in which regioselective O-methanesulfonatio n and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo-phytosphingosinetype glycolipi ds 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindros ides, were efficiently synthesized in a stereocontrolled manner. (C) 1999 E lsevier Science Ltd. All rights reserved.