HCID 69624823, compound → HCID 69624850, compound

Participants

Reaction Conditions

Reaction Steps

First, 5.85 g (7.33 mmol) 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]was dissolved in toluene (500 ml). Then, 0.70 g (3.68 mmol) of paratoluene sulfate monohydrate was added to the mixture and stirred at about 100° C. for about 1 hour. After the reaction was terminated, a saturated solution of sodium hydrogen carbonate in water was added to the reaction mixture which was then subjected to extraction with diethylether. The ether solution was washed with saturated saline and 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: dichloromethane] to give 3.31 g (yield 58%) of (1R)-1,5-anhydro-1-C-[1-(phenylsulfonyl)indole-2-yl]-2,3,4,6-tetra-O-benzyl-D-mannitol [compound (VI) wherein R1 to R4 are benzyl and R5 is phenylsulfonyl].

Provenance & Evidence