Synthesis of substituted fatty oxathiolanes and thioethers from an allylic oxo fatty acid ester |
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Authors: | S Afaque M H Ansari M S Ahmad M S Siddiqui |
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Affiliation: | 1. Department of Chemistry, Aligarh Muslim University, 202 002, Aligarh, India
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Abstract: | 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. |
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