The 6-O-trityl derivative of 2,3:5,6:3',4'-O-isopropylidenelactose dimethyl acetal (1) was converted through an oxidation/oximation/reduction sequence involving the free 2-OH group of the D-galactose moiety into the protected disaccharide 5 in up to 75% yield. The complete deprotection of 5 produced the disaccharide 4-O-(2-acetamido-2-deoxy-beta-D-talopyranosy)-D-glucose glucose (7a). The oxime LiAlH4 reduction step produced some unexpected side-products, the most abundant of which, the dimethyl acetal 9, deriving from cleavage of the D-glucose moiety, was formed only when the reaction was conducted in refluxing THF, but not when Et2O was used as the solvent.
|Autori interni:||CATELANI, GIORGIO|
|Autori:||BARILI P.L.; BERTI G.; CATELANI G; D'ANDREA F.; PUCCIONI L.|
|Titolo:||Stereoselective synthesis of 4-O-(2-acetamido-2-deoxy-beta-D-talopyranosyl)-D-glucose derivatives from lactose|
|Anno del prodotto:||2000|
|Digital Object Identifier (DOI):||10.1080/07328300008544066|
|Appare nelle tipologie:||1.1 Articolo in rivista|