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A Rapid and Efficient Synthesis of D ‐ erythro ‐Sphingosine from D ‐ ribo ‐Phytosphingosine
Author(s) -
van den Berg Richard J. B. H. N.,
van den Elst Hans,
Korevaar Cornelius G. N.,
Aerts Johannes M. F. G.,
van der Marel Gijsbert A.,
Overkleeft Herman S.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100911
Subject(s) - sphingosine , chemistry , sphingolipid , ceramide , diastereomer , stereochemistry , biochemistry , receptor , apoptosis
In this paper we describe the concise synthesis of D ‐ erythro ‐sphingosine starting from the readily available chiral building block D ‐ ribo ‐phytosphingosine. The title compound is the ubiquitous sphingolipid from which most mammalian ceramides are derived. Our work is based on the existing literature in which the same sphingoid base is used as a starting point and culminates in what we believe is the most efficient synthesis of D ‐ erythro ‐sphingosine reported to date.