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A convenient one‐pot synthesis of 2,5‐anhydro‐3,4,6‐tri‐O‐benzoyl‐D‐[1‐ 14 C]allononitrile, and its conversion to methyl 2‐β‐D‐ribofuranosyl‐4‐[2‐ 14 C]selenazolecarboxylate
Author(s) -
Woo Peter W. K.
Publication year - 1988
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.2580251013
Subject(s) - chemistry , sodium methoxide , sodium iodide , medicinal chemistry , potassium cyanide , methyl iodide , sodium , methanol , potassium , selenide , cyanide , organic chemistry , selenium
Reaction of 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose ( 3 ) with [ 14 C]cyanotrimethylsilane, generated in situ by reaction of potassium [ 14 C]cyanide and chlorotrimethylsilane in the presence of sodium iodide and 2,6‐lutidine, gave 2,5‐anhydro‐3,4,6‐tri‐O‐benzoyl‐D‐[1‐ 14 C]allononitrile ( 4 ). Sequential reaction of the latter with hydrogen selenide, ethyl bromopyruvate, and methanolic sodium methoxide gave methyl β‐D‐ribofuranosyl‐4‐[2‐ 14 C]selenazolcarboxylate ( 7 ), penultimate precursor to [2‐ 14 C]CI‐935, or 2‐β‐D‐ribofuranosyl‐4‐[2‐ 14 C]selenazolecarboxamide ( 8 ).