| 主权项 |
1. A method for synthesizing D-erythro-sphingosine, comprising the steps of:
a) protecting the amino group of an L-serine ester having the following structure:wherein R is a C1-5 alkyl group, or a salt thereof, with a tert-butoxycarbonyl group, resulting in a Boc-protected L-serine ester;
b) allowing the Boc-protected L-serine ester to react with 2,2-dimethoxypropane in the presence of benzenesulfonic acid under conditions effective to yield the corresponding C1-C5 alkyl ester of (S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidincarboxylic acid; c) allowing the corresponding C1-C5 alkyl ester of (S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidincarboxylic acid to react with dimethyl methylphosponate in the presence of n-butyllithium under conditions effective to yield (S)-3-(tert-butoxycarbonyl)-4-(2-(dimethoxy-phosphoryl)-1-oxo-ethyl)-2,2-dimethyloxazolidine; d) allowing (S)-3-(tert-butoxycarbonyl)-4-(2-(dimethoxy-phosphoryl)-1-oxo-ethyl)-2,2-dimethyloxazolidine to react with 1-tetradecanal under conditions effective to yield (S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine; e) allowing (S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine to react with sodium borohydride and cerium trichloride under conditions effective to yield (2S,3R,4E)-3-(tert-butoxycarbonyl)-4-(1-hydroxy-hexadec-2-enyl)-2,2-dimethyloxazolidine; and f) removing the tert-butoxycarbonyl (Boc) protecting group of (2S,3R,4E)-3-(tert-butoxycarbonyl)-4-(1-hydroxy-hexadec-2-enyl)-2,2-dimethyloxazolidine under conditions effective to yield D-erythro-sphingosine. |
