The formation of symmetrical glycuronates by oxidation of methyl α-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 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. OI sindona, giovanni/0000-0002-5623-5795
The formation of symmetrical glycosyl glycuronates by direct oxidation of partially protected methyl alpha-D-glycopyranosides
De Nino A;DALPOZZO, Renato;MAIUOLO, Loredana;SINDONA, Giovanni
2002-01-01
Abstract
The formation of symmetrical glycuronates by oxidation of methyl α-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
