Chirospecific Synthesis of D-erythro- and L-threo-Sphinganines from Sugars

Abstract

D-erythro-sphinganine 1 and L-threo-sphinganine 2 have been prepared in the enantiomerically pure form by the chirospecific manner. Key intermediates, 2-amino-3-hydroxy-4-pentenoates 8 and 12, were obtained from L-glucono-1,5-lactone and L-gulonic acid g-lactone via a simultaneous dealkoxyhalogenation.

Sphingolipid Synthesis via Olefin Cross Metathesis: Preparation of a Differentially Protected Building Block and Application to the Synthesis of d-erythro-Ceramide

“…Gargano and Lees have reported the preparation of an orthogonally protected sphingosine with the main carbon chain already installed; See ref c.…”

“…Sphingolipids are involved in molecular recognition processes at the cell membrane and are important components of lipid rafts and influence cell signaling events at the membrane. As a result of our interest in glycosphingolipid recognition processes, we sought a general synthetic route to sphingolipids that would allow systematic variation of both the O- and N-linked functionalities, as well as the identity of the main carbon chain . In practice, this requires the preparation of a building block such as I , which contains all of the conserved and requisite functionality differentiated with orthogonal protecting groups…”