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Synthesis of carbon‐14 labeled Taxol® (paclitaxel)
Author(s) -
Walker Donald G.,
Swigor John E.,
Kant Joydeep,
Schroeder Daniel R.
Publication year - 1994
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.2580341010
Subject(s) - chemistry , paclitaxel , regioselectivity , silylation , chloride , cleavage (geology) , benzoyl chloride , side chain , stereochemistry , medicinal chemistry , organic chemistry , catalysis , chemotherapy , medicine , polymer , surgery , geotechnical engineering , fracture (geology) , engineering
Reductive cleavage of the C13 side chain of Taxol® (1, paclitaxel) followed by regioselective silylation gave 7‐triethylsilylbaccatin III (4). 3‐O‐Triethylsilylation of 5 and subsequent reaction with benzoyl chloride‐ C 7‐ 14 C gave azetidinone 7. Coupling of 4 and 7 followed by deprotection gave 1.26 g of Taxol®‐ N 3′‐ 14 C (11) having a specific activity of 26.5 mCi/mmol and a radiochemical purity of 95%.