20702-87-8Relevant academic research and scientific papers
Convenient preparation of L-arabino-hexos-5-ulose derivatives from lactose
Catelani, Giorgio,Corsaro, Antonino,D'Andrea, Felicia,Mariani, Manuela,Pistara, Venerando,Vittorino, Elisa
, p. 2349 - 2358 (2007/10/03)
2,6-Di-O-benzyl- (9), 2-O-benzyl-3,4-O-isopropylidene- (19), and 2-O-benzyl-6-O-m-chlorobenzoyl-L-arabino-hexos-5-ulose (20) have been prepared using 4′-deoxy-4′-eno- and 6′-deoxy-5′-eno lactose dimethyl acetal derivatives 7 and 14 as key intermediates. The synthesis of enol ethers 7 and 14 has been performed with good yields by base-promoted elimination of acetone or p-toluenesulfonic acid from 2′,6′-di-O- benzyl-, and 6′-O-p-toluenesulfonyl-2,3:5,6:3′,4′-tri-O- isopropylidenelactose dimethyl acetal, respectively. The epoxidation with MCPBA of 7 and 14 in methanol or dichloromethane furnishes C-5′-methoxy and C-5′-m-chlorobenzoyloxy derivatives, easily transformed with good yields into L-arabino 5-ketoaldohexoses 9, 19 and 20.
Stereoselective synthesis of 4-O-(2-acetamido-2-deoxy-β-D-talopyranosyl)-D-glucose derivatives from lactose
Barili, Pier Luigi,Berti, Giancarlo,Catelani, Giorgio,D'Andrea, Felicia,Puccioni, Leonardo
, p. 79 - 91 (2007/10/03)
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% y
