Sulfuric Acid → HCID 54149222, compound

Participants

Reaction Steps

The hydrolysis of methyl 2,3,4,6-tetra-O-benzyl-L-glucopyranoside may be carried out in glacial acetic acid and dilute sulphuric acid as formulated by Tate and Bishop (supra) to produce 2,3,4,6-tetra-O-benzyl-L-glucopyranose which can be reacted with thionyl chloride to form 2,3,4,6-tetra-O-benzyl-L-glucopyranosyl chloride. Halogenation of 2,3,4,6-tetra-O-benzyl-L-glucopyranose with zinc chloride-thionyl chloride results in a homogeneous 2,3,4,6-tetra-O-benzyl α-L-glucopyranosyl chloride product. In an alternative procedure, methyl 2,3,4,6-tetra-O-benzyl-α-L-glucopyranoside may be refluxed with thionyl chloride (48 hours at 5° C.) to produce 2,3,4,6-tetra-O-benzyl-L-glucopyranosyl chloride.

Provenance & Evidence