An efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenine and related compounds from 2-amino-2-deoxy-D-glucose.
Efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenines having C16, C18, and C20 carbon-chains was achieved in 13 steps, starting from allyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. 2-Amino-1,6-di-O-tert- butyldiphenylsilyl-2-N,3-O-carbonyl-2-deoxy-D -allitol was used as the key intermediate.
Sugawara
T
T
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
Narisada
M
M
D002236:Carbohydrate Conformation; D005944:Glucosamine; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009904:Optical Rotation; D013110:Sphingosine / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D005944:Glucosamine; D013110:Sphingosine