Potassium Sodium Tartrate → HCID 69624823, compound

Participants

Reaction Conditions

Reaction Steps

First, 7.74 g (9.72 mmol) of 1-C-[1-(phenylsulfonyl)indole-2-yl]-2,3,4,6-tetra-O-benzyl-D-mannopyranose [compound (IV) wherein R1 to R4 are benzyl and R5 is phenylsulfonyl] was dissolved in tetrahydrofuran (240 ml). Then, 1.11 g (29.25 mmol) of lithium aluminum hydride was added to the mixture and stirred at about 0° C. for about 30 minutes. After the reaction was completed, a saturated aqueous solution of Rochelle salt was added to the reaction mixture which was then subjected to extraction with diethylether. The ether solution was washed with saturated saline and then dried on anhydrous sodium sulfate. After removal of the solvent by distillation, the residue was fractionated by column chromatography on silica gel [silica gel: Merck Kieselgel 60 (230-400 mesh ASTM); elution solvent: n-hexane and ethyl acetate (5:2)] to give 5.85 g (yield 75%) of 1-C-[1-(phenylsulfonyl)indole-2-yl]-2,3,4,6-tetra-O-benzyl-D-mannitol [compound (V) wherein R1 to R4 are benzyl and R5 is phenylsulfonyl].

Provenance & Evidence