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.