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Chemical synthesis of allyl‐[ 13 C 6 ]‐glucuronate
Author(s) -
Latli Bachir,
Hrapchak Matt,
Seetharama Ravikumar,
Krishnamurthy Dhileepkumar,
Senanayake Chris H.
Publication year - 2011
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.1875
Subject(s) - chemistry , glucuronate , organic chemistry , stereochemistry , biochemistry
The synthesis of allyl‐[ 13 C 6 ]‐glucuronate from α ‐D‐[ 13 C 6 ]‐glucose in five steps is described. Selective protection of the primary alcohol in the glucose with the bulky trityl group followed by acetylation in the same pot gave the fully protected sugar. Removal of the trityl group followed by oxidation of the primary alcohol to the acid and removal of the acetate groups using catalytic amounts of sodium methoxide gave the glucuronic acid. Reaction with allyl bromide using resin‐bound fluoride gave the title compound. Copyright © 2011 John Wiley & Sons, Ltd.