Premium
Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer‐supported triphenylphosphine: synthesis of protected (2 S , 3 S )‐[3‐ 2 H, 15 N]‐tyrosine
Author(s) -
Barnett Derek W.,
Refaei Maryanne S.,
Curley Robert W.
Publication year - 2013
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.3004
Subject(s) - chemistry , triphenylphosphine , benzyl chloride , deuterium , yield (engineering) , alkylation , organic chemistry , medicinal chemistry , catalysis , physics , materials science , quantum mechanics , metallurgy
Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer‐supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α ‐carbon and 82% de at the β ‐carbon. Key in the synthesis was the alkylation of 15 N‐labeled (−)‐8‐phenylmenthylhippurate with R ‐(−)‐4‐triisopropylsilyloxybenzyl‐ α‐d chloride.