Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides

DOI: 10.1016/S0040-4020(98)01104-1

Source and publish data:

Tetrahedron p. 989 - 1004 (1999)

Update date:2022-08-03

Topics:

Authors:

Murakami, Teiichi

Taguchi, Kazuhiro

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Article abstract of DOI:10.1016/S0040-4020(98)01104-1

D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl- D-glucosamine 3 by an improved route in which regioselective O- methanesulfonation and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo- phytosphingosine-type glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereocontrolled manner.

Full text of DOI:10.1016/S0040-4020(98)01104-1

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