A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs.
Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-D-erythro structures in good yields.
Cai
Ye
Y
Alberta Ingenuity Center for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
Ling
Chang-Chun
CC
Bundle
David R
DR
D019496:Cancer Vaccines / Q000138:chemical synthesis; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D008968:Molecular Conformation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D019496:Cancer Vaccines; D007202:Indicators and Reagents; C012491:phytosphingosine; D013110:Sphingosine; C005682:safingol