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The synthesis of C-13 labeled vitamin E, [12′-13C] all-rac-α-tocopherol

✍ Scribed by Shiro Urano; Shun-Ichiro Nakano; Mitsuyoshi Matsuo

Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
312 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis

12 '-13C] aZZ-rac-a-Tocopherol (L) was synthesized from [2-13C] acetone. The condensation of 6-methoxymethoxy-2,5,7,8-tetramethyl-2-(5-mercaptothiazolinyl-4-methyl-3-penten-1-y1)chroman (S) with [7-Clgeranyl bromide (11, which was prepared by the coupling of (6-benzoyloxy--4-methyl-4-hexenyl)triphenylphosphonium bromide (2) with [2-13C]acetone following bromination, afforded [121-13C] 6-methoxymethoxy-2,5,7,8-tetramethyl-2- [(3E,7E,9E)-5-mercaptoth~azol~nyl-4,8,12-trimethyl-3,7,9tridecatrien-1-y1)chroman (2). After desulfurization and reduction of 9, the reaction product obtained was converted into [12'-13C]aZZ-rac-a-tocopherol (1)byhydrolysis. The total yield of 1 was 3 3 . 7 % on the basis of [2-13C]acetone.

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