Methane → HCID 21219056, compound

Participants

Reaction Steps

To a suspension of 3 g of castanospermine in 30 ml of pyridine at 0° C. was added dropwise a solution of 3 g of 4-methylbenzoyl chloride. After the addition, the mixture was allowed to warm to room temperature and then heated at 55° C. for 24 hours. The reaction mixture was diluted with 10 ml of water and evaporated to dryness in vacuo. The resulting residue was stirred in 150 ml of a 1:2 mixture of water:methylene chloride. The insoluble material was separated by filtration to provide an amorphous off-white solid which was dissolved in 60 ml of hot methanol, treated with 0.5 g of activated charcoal and filtered. The colorless liltrate was cooled to give colorless crystals of [1S-(1α, 6β, 7α, 8β, 8αβ)]-octahydro-1,6,7,8-indolizine-tetrol 6-(4-methylbenzoate) melting at about 255°-258° C. with decomposition (580 mg, 12% yield).

Provenance & Evidence