Water → HCID 15699537, compound

Participants

Reaction Steps

Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside (6 g, 37 mmol) in dry pyridine (50 ml) was treated with toluene-p-sulphonyl chloride (15.2 g, 80 mmol) at 0° with stirring. The reaction mixture was stored at 22° for 12 h, and after the addition of water (1 ml) it was concentrated. The syrupy residue was poured into ice-water, the oil which separated was extracted with CHCl3, and the extracts were washed with water, dried and evaporated. The solid thus obtained (12 g, 70%) was recrystallized from methanol to give pure methyl 2,3-dideoxy-4,6-di-O-toluene-p-sulphonyl-α-D-erythro-hexopyranoside. M.p.: 110°-111.5°. [α]D22 +80.8° (c 1, chloroform).

Provenance & Evidence