F. Compernolle
Nov 15, 1980
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Journal
Carbohydrate Research
Abstract
Abstract Allyl 2,3,4-tri- O -allyl- d -glucopyranuronate (7) has been prepared (overall yield, 37%) from methyl 1,2,3,4-tetra- O -acetyl-α- or -β- d -glucopyranuronate via a six-step reaction procedure. 1- O -Acetyl-, 1- O -methacryloyl-, and 1- O -phenylacetyl-αβ- d -glucopyranuronic acid are produced by esterification of 7 and removal of the allyl groups with palladium-on-carbon in an acidic medium. The reaction of 7 with the di-imidazole derivative of bilirubin yields the allyl-protected mono- and di- d -glucopyranosyluronic acid derivatives of bilirubin. Neither the bilirubin nor the corresponding biliverdin derivatives resisted the conditions required for de-allylation.