Synthesis of an l-quinovose-containing disaccharide

Synthesis of l-Hexoses

“…The selectivity was explained by the hydride attacking from the opposite side of the bulky and axial anomeric substituent . A disaccharide containing 6-deoxy- l -glucose has also been synthesized from the corresponding 3- O -benzoyl 2-uloside by stereoselective reduction …”

“…399 disaccharide containing 6-deoxy-L-glucose has also been synthesized from the corresponding 3-O-benzoyl 2-uloside by stereoselective reduction. 402 Stereoselective reduction of 3-ulosides has been used to prepare 6-deoxy-L-altrosides. 235,403−406 For instance, L-rhamnoside 541 was oxidized to 3-uloside 542 followed by stereoselective reduction with NaBH 4 to give 543 having an axial C3 substituent (Scheme 82a).…”