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 | Zendy

Barnett Derek W. | Zendy; Refaei Maryanne S. | Zendy; Curley Robert W. | Zendy

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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.

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