The formation of symmetrical glycuronates by oxidation of methyl alpha-D-2,3,4-tri-O-benzoyl glycopyranosides with pyridine dichlorochromate is described. A key intermediate in the process is represented by the initially formed aldehydes which react further through two competing reaction pathways leading to the glycals and to the symmetrical esters. The symmetrical glycuronates are formed by oxidation of the corresponding hemiacetal intermediates. The absolute configuration of the chiral centers at position 2-, 3-, and 4- of the glycopyranosides does not affect the two competing reaction paths.
The formation of symmetrical glycosyl glucuronates by direct oxidation of partially protected methyl alfa-D-glycopyranosides
DE NINO, Antonio;CUPONE G;DALPOZZO R;
2002-01-01
Abstract
The formation of symmetrical glycuronates by oxidation of methyl alpha-D-2,3,4-tri-O-benzoyl glycopyranosides with pyridine dichlorochromate is described. A key intermediate in the process is represented by the initially formed aldehydes which react further through two competing reaction pathways leading to the glycals and to the symmetrical esters. The symmetrical glycuronates are formed by oxidation of the corresponding hemiacetal intermediates. The absolute configuration of the chiral centers at position 2-, 3-, and 4- of the glycopyranosides does not affect the two competing reaction paths.File in questo prodotto:
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