A FACILE STEREODIVERGENT SYNTHESIS OF THREO-N,N-DIBENZYL AND ERYTHRO-N,N-DIBENZYL SPHINGOSINES FROM (S)-N,N-DIBENZYL-O-TBDMS-SERINAL

Authors
ANDRES JM PEDROSA R
Citation
Jm. Andres et R. Pedrosa, A FACILE STEREODIVERGENT SYNTHESIS OF THREO-N,N-DIBENZYL AND ERYTHRO-N,N-DIBENZYL SPHINGOSINES FROM (S)-N,N-DIBENZYL-O-TBDMS-SERINAL, Tetrahedron : asymmetry, 9(14), 1998, pp. 2493-2498
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
14
Year of publication
1998
Pages
2493 - 2498
Database
ISI
SICI code
0957-4166(1998)9:14<2493:AFSSOT>2.0.ZU;2-N
Abstract
The (L)-threo-N,N-dibenzyl sphingosine was prepared in two steps from the serinal derivative 1 by diastereoselective alkenylation with penta dec-l-enyl(ethyl)zinc and deblocking. (D)-erythro-N,N-Dibenzyl sphingo sine was also prepared in two steps from 1 by a highly diastereoselect ive alkynylation with pentadecynyl magnesium bromide and subsequent st ereoselective LAH reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.