2,3'-Anhydrosucrose

Article abstract of DOI:10.1016/0008-6215(90)80136-Q

Alkine hydrolysis of α-D-glucopyranosyl 3,4-anhydro-β-D-ribo-hexulofuranoside (1) involves participation of HO-2 and leads to 2,3'-anhydrosucrose (2).The structure of 2 was assigned on the basis of the n.m.r. and mass spectra of its hexa-acetate 3 and confirmed by the formation from 2 of the 6,6'-di- (4) and 6,1',6'-tri-O-trityl (5) derivatives, the 4,6-O-isopropylidene derivative (6), and 2,3':3,4-dianhydro-galacto-sucrose, isolated as the tetra-acetate 7.The structure of 7 was confirmed by its conversion into the 4'-O-tosyl-6,1',6'-tri-O-trityl derivative 14 and by unambiguous synthesis from 6.