Aluminum → HCID 69624706, compound

Participants

Reaction Conditions

Reaction Steps

First, 1.73 g (2.25 mmol) of 2-hydroxyimino-3-[2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)indole-3-yl]propionic acid ethyl ester [compound (IX) wherein R1 to R4 are benzyl and R6 is ethyl] was dissolved in tetrahydrofuran (225 ml)-water (25 ml). Then, aluminum amalgam prepared from 8.50 g (0.32 mmol) of aluminum was added to the mixture and stirred at 55° C. for about 0.5 hour. Then, the reacted solution was filtrated on Celite which was then washed with 10% ethanol-dichloromethane. The filtrate was then concentrated and the residue was fractionated by column chromatography on silica gel [silica gel: Merck Kieselgel 60 (230-400 mesh ASTM); elution solvent: 3% methanol-dichloromethane] to give 1.54 g (yield 90%) of 2-amino-3-[2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)indole-3-yl]propionic acid ethyl ester [compound (x) wherein R1 to R4 are benzyl and R6 is ethyl].

Provenance & Evidence