2,3′-anhydrosucrose

Abstract

Alkaline 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.