N,N',N"-Tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy]phenyl]-1,3,5-benzenetrisulfonamide → N,N',N"-Tris[4-[(4-O-alpha-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]phenyl]-1,3,5-benzenetrisulfonamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 800 mg of N,N',N"-tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]phenyl]-1,3,5-benzenetrisulfonamide in 15 ml of methanol was cooled in an ice-water bath, then ammonia was bubbled in, with stirring for one hour. The cooling bath was removed and stirring was continued for 4 days. The solvents were evaporated and the residue was heated in vacuo at 110° C. for 2 hours. This residue was crystallized from a mixture of methanol and ethanol, giving 280 mg of the desired intermediate as a white powder, mp 206°-210° C.

Provenance & Evidence