Literature DB >> 19766990

Efficient synthesis of D-xylo and D-ribo-phytosphingosines from methyl 2-amino-2-deoxy-beta-D-hexopyranosides.

Ye Cai1, Chang-Chun Ling, David R Bundle.   

Abstract

A general and flexible synthetic approach to biologically important 5,6-unsaturated C(18)-phytosphingosines was developed via olefin cross-metathesis employing truncated C(6)-phytosphingosines as the key intermediates. These were efficiently prepared in high yields by zinc-mediated reductive opening of methyl 2-amino-2-deoxy-beta-hexopyranosides. [structure: see text]

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Year:  2009        PMID: 19766990     DOI: 10.1016/j.carres.2009.07.007

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  1 in total

1.  Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-sphinganine, (+)-spisulosine, and D-ribo-phytosphingosine.

Authors:  Ewen D D Calder; Ahmed M Zaed; Andrew Sutherland
Journal:  J Org Chem       Date:  2013-07-03       Impact factor: 4.354

  1 in total

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