The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2',6'-di-O-benzyl-2,3:3',4'-di-O-isopropylidenelactose dimethyl acetal (1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups

Chemical transformation of lactose into 4-O-beta-D-galactopyranosyl-D-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof

D'ANDREA, FELICIA;CATELANI, GIORGIO;
2002

Abstract

The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2',6'-di-O-benzyl-2,3:3',4'-di-O-isopropylidenelactose dimethyl acetal (1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups
Attolino, E; D'Andrea, Felicia; Catelani, Giorgio; Puccioni, L.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/205807
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