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 ptoluenesulfonic 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?-mchlorobenzoyloxy derivatives, easily transformed with good yields into L-arabino 5-ketoaldohexoses 9, 19 and 20.

Convenient preparation of L-arabino-hexos-5-ulose derivatives from lactose

CATELANI, GIORGIO;D'ANDREA, FELICIA;
2003

Abstract

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 ptoluenesulfonic 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?-mchlorobenzoyloxy derivatives, easily transformed with good yields into L-arabino 5-ketoaldohexoses 9, 19 and 20.
Catelani, Giorgio; Corsaro, A; D'Andrea, Felicia; Mariani, M; Pistara', V; Vittorino, E.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/187942
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