Efficient synthesis of D-xylo and D-ribo-phytosphingosines from methyl 2-amino-2-deoxy-beta-D-hexopyranosides.
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]
Cai
Ye
Y
Alberta Ingenuity Center for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, AB, Canada T6G 2G2.
Ling
Chang-Chun
CC
Bundle
David R
DR
D008759:Methylglycosides / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C521790:D-ribo-phytosphingosine; D008759:Methylglycosides; C458140:xylo-phytosphingosine; D013110:Sphingosine