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Synthesis of [2,3,3,2′,3′,5′,6′‐ 2 H 7 ]‐L‐tyrosine from phenol‐ d 6
Author(s) -
Kendall John T.
Publication year - 2000
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 - 10.1002/1099-1344(200008)43:9<917::aid-jlcr377>3.0.co;2-5
Subject(s) - chemistry , enantioselective synthesis , phenol , tyrosine , olefin fiber , acrylic acid , stereochemistry , amino acid , organic chemistry , catalysis , biochemistry , polymer , monomer
An enantioselective synthesis of [2,3,3,2′,3′,5′,6′‐ 2 H 7 ]‐L‐tyrosine is described. Z ‐3‐(4‐acetoxy‐2,3,5,6‐ 2 H 4 ‐phenyl)‐3‐ 2 H‐2‐acetylamino acrylic acid was prepared in five steps from phenol‐ d 6 . Chiral reduction of the olefin followed by removal of the acetate protecting groups furnished the d 7 ‐amino acid in high ee. Copyright © 2000 John Wiley & Sons, Ltd.