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Synthesis of substituted fatty oxathiolanes and thioethers from an allylic oxo fatty acid ester
Author(s) -
Afaque S.,
Ansari M. H.,
Ahmad M. S.,
Siddiqui M. S.
Publication year - 1989
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf03022758
Subject(s) - thioether , diol , chemistry , allylic rearrangement , hydroxymethyl , fatty acid , methyl oleate , stereochemistry , catalysis , organic chemistry
Substituted oxathiolane and thioether derivatives have been synthesized from an allylic oxo fatty acid ester. The reaction of methyl 4‐oxo‐ trans ‐2‐octadecenoate with 3‐mercaptopropan‐1,2‐diol (1‐thioglycerol) affords methyl 4‐(3′‐hydroxymethyl‐1′,4′‐oxathiolane)‐2(3)‐(O‐mercaptopropan‐1″,2″‐diol)‐octadecanoate (II), methyl 4‐oxo‐2(3)‐(O‐mercaptopropan‐1′,2′‐diol)‐octadecanoate (III), methyl 4‐(3′‐hydroxy‐l′,5′‐oxathiane)‐2 (3)‐(S‐mercaptopropan‐1″,2″‐diol)‐octadecanoate (IV), methyl 4‐oxo‐2(3)‐(S‐mercaptopropan‐1′, 2′diol)‐octadecanoate (V) and methyl 4‐(3′‐hydroxymethyl‐1′, 4′‐oxathiolane)‐2(3)‐(S‐mercaptopropan‐1″, 2″‐diol)‐octadecanoate (VI). Structures of the individual reaction products have been established on the basis of spectral data and microanalyses.