Protected sphingosine from phytosphingosine as an efficient acceptor in glycosylation reaction

Organic Letters
Roberta Di BenedettoLuigi Panza

Abstract

A convenient, simple, and high-yielding five-step synthesis of a sphingosine acceptor from phytosphingosine is reported, and its behavior in glycosylation reactions is described. Different synthetic paths to sphingosine acceptors using tetrachlorophthalimide as a protecting group for the sphingosine amino function and different glycosylation methods have been explored. Among the acceptors tested, the easiest accessible acceptor, unprotected on the two hydroxyl groups in positions 1 and 3, was regioselectively glycosylated on the primary position, the regioselectivity depending on the donor used.

References

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Citations

May 17, 2017·Chemical Communications : Chem Comm·Kyan A D'Angelo, Mark S Taylor
Feb 15, 2018·Organic Letters·Hiromichi EgamiYoshitaka Hamashima

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