Tributylstannane → HCID 14057275, compound

Participants

Reaction Steps

To a solution of methyl 6-deoxy-3-O-phenylthiono-formyl-α-L-mannopyranoside, 2,4-O-dibenzoate (3.5 g, 6.7 mmol) in toluene (120 mL) is added AIBN (55 mg, 0.34 mmol) and n-Bu3SnH (2.6 mL, 13.4 mmol). The solution is deoxygenated by passing through N2 gas for 20 min. The reaction flask is placed in an oil bath (120° C.). After 1.5 h TLC indicates that the reaction is complete. Evaporation of the solvent yields a residue. Purification by chromatography (eluting with hexane/ethyl acetate in gradient from 500:20 to 500:50) yields methyl 3,6-dideoxy-α-L-mannopyranoside, 2,4-O-dibenzoate (1.8 g, 70% in two steps from 6-deoxy-α-L-mannopyranoside, 2,4-O-dibenzoate).

Provenance & Evidence