Linked Life Data

12530859

Source:http://linkedlifedata.com/resource/pubmed/id/12530859

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
2
pubmed:dateCreated
2003-1-17
pubmed:abstractText
6-Hydroxy-(4E)-sphingenine-containing ceramides were found recently in human skin. We present here the first synthesis of the 6S and 6R diastereoisomers 2 and 3, which represent analogues of (2S,3R)-ceramide (1) having two allylic hydroxyl groups. Chiral propargylic alcohols 8 and 11, which were prepared by asymmetric dihydroxylation of alpha,beta-unsaturated ester 13 and allylic chloride 22, respectively, were employed as precursors of 2 and 3. Nucleophilic addition of lithiated TBS-protected propargylic ethers 25 and 32 to l-serine-derived aldehyde 26, respectively, afforded oxazolidine intermediates 27 and 33. Acid-mediated deprotection of the oxazolidine, followed by N-acylation and Birch reduction, completed the syntheses of 2 and 3.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
24
pubmed:volume
68
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
348-54
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
2003
pubmed:articleTitle
First asymmetric synthesis of 6-hydroxy-4-sphingenine-containing ceramides. Use of chiral propargylic alcohols to prepare a lipid found in human skin.
pubmed:affiliation
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing 11367-1597, USA.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.