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Synthesis of [2S-2-2H]- and [2R-2-2H]hexadecanoic acids

✍ Scribed by A.P. Tulloch

Publisher
Elsevier Science
Year
1982
Tongue
English
Weight
608 KB
Volume
30
Category
Article
ISSN
0009-3084

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✦ Synopsis

2S-2-2H]-and [ 2R-2-2H] hexadecanoic acids were synthesized in overall yields of 59-67%. Methyl(2R)-2-hydroxyhexadecanoate, from the acid produced by Hansenula sydowiorum, was converted to the p-toluenesulphonate, reduced to trideutero alcohol with lithium aluminum deuteride and oxidized to [2S-2-2H]hexadecanoic acid. Methyl (2S)-2-chlorohexadecanoate, which was a by-product of tosylation and was also prepared by chlorination of the hydroxy ester with thionyl chloride, on reduction and oxidation as before gave [2R-2-2H]hexadecanoic acid. Intermediates were fully characterized, isotopic purity was 97% and optical purity was maintained throughout the syntheses. Attempts to reduce the tosyl or chloro groups, only, with sodium borodeuteride gave low yields probably due to preferential reduction of the ester group; 1,2-epoxyhexadecane was obtained from the tosylate and 2-chlorohexadecan-l-ol from the chloro ester.

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