Lactose as an inexpensive starting material for the preparation of aldohexos-5-uloses: synthesis of L-ribo and D-lyxo derivatives.
Partially protected derivatives of L-ribo- and D-lyxo-aldohexos-5-ulose have been prepared starting from triacetonlactose dimethyl acetal derivatives. Key steps of the synthetic sequences are (a) the synthesis of 4'-deoxy-4'-eno- and 6'-deoxy-5'-eno lactose derivatives, and (b) the epoxidation-methanolysis of the above-mentioned enol ethers to give 1,5-bis-glycopyranosides, masked form of the target 1,5-dicarbonyl hexoses.
Guazzelli
Lorenzo
L
Dipartimento di Scienze Farmaceutiche, Università di Pisa, Via Bonanno, 33 I-56126 Pisa, Italy.
Catelani
Giorgio
G
D'Andrea
Felicia
F
D006601:Hexoses / Q000138:chemical synthesis*; D007785:Lactose / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism
D006601:Hexoses; D007785:Lactose