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Preparation of specifically dideuterated octadecanoates and oxooctadecanoates
Author(s) -
Tulloch A. P.
Publication year - 1977
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532978
Subject(s) - chemistry , sodium cyanoborohydride , deuterium , sodium , lithium (medication) , nuclear chemistry , medicinal chemistry , organic chemistry , medicine , physics , quantum mechanics , endocrinology
Sixteen methyl gem dideuterooctadecanoates with two deuterium atoms at positions 2‐ to 17‐ and seven oxo esters, 8‐oxooctadecanoate‐5,5‐ d 2 , 8‐oxooctadecanoate‐11,11‐ d 2 , 11‐oxooctadecanoate‐8,8‐ d 2 , 11‐oxooctadecanoate‐14,14‐ d 2 , 12‐oxooctadecanoate‐9,9‐ d 2 , 7‐oxooctadecanoate‐10,10‐ d 2 and 13‐oxooctadecanoate‐16,16‐ d 2 with two deuteriums on the carbon γ to the oxo group, have been synthesized. Two principal methods of introducing deuterium were used: preparation of 2,2‐dideutero acids by exchange with deuterium oxide followed by chain extension giving dideuteroxooctadecanoates, which were then reduced, as tosylhydrazones, with sodium cyanoborohydride to dideuterooctadecanoates and stepwise introduction by reduction of oxooctadecanoates with sodium borodeuteride, formation of tosylate or mesylate, reduction with lithium aluminium deuteride to tetradeuterooctadecanol and oxidation to dideuterooctadecanoic acid.