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The synthesis of C‐13 labeled vitamin E, [12′‐ 13 C] all‐rac ‐α‐tocopherol
Author(s) -
Urano Shiro,
Nakano ShunIchiro,
Matsuo Mitsuyoshi
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210405
Subject(s) - chemistry , acetone , halogenation , bromide , yield (engineering) , hydrolysis , bromine , tocopherol , organic chemistry , medicinal chemistry , vitamin e , antioxidant , materials science , metallurgy
[12′‐ 13 C] all‐rac ‐α‐Tocopherol ( 1 ) was synthesized from [2‐ 13 C]acetone. The condensation of 6‐methoxymethoxy‐2,5,7,8‐tetramethyl‐2‐(5‐mercaptothiazolinyl‐4‐methyl‐3‐penten‐1‐yl)chroman ( 8 ) with [7‐ 13 C]geranyl bromide ( 7 ), which was prepared by the coupling of (6‐benzoyloxy‐4‐methyl‐4‐hexenyl)triphenylphosphonium bromide ( 5 ) with [2‐ 13 C]acetone following bromination, afforded [12′‐ 13 C]6‐methoxymethoxy‐2,5,7,8‐tetramethyl‐2‐(3E,7E,9E)‐5‐mercaptothiazolinyl‐(4,8,12‐trimethyl‐3,7,9‐tridecatrien‐1‐yl) chroman ( 9 ). After desulfurization and reduction of 9 , the reaction product obtained was converted into [12′‐ 13 C] all‐rac ‐α‐tocopherol ( 1 ) by hydrolysis. The total yield of 1 was 33.7% on the basis of [2‐ 13 C]acetone.