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The building block of N-alkyl derivative of allosamidin(chitinase inhibitor),4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride was stereoselectively synthesized in two steps under mild conditions.Nucleophilic addition of octylamine to 2- oxoglucopyranoside gave a‘carbonyl group transfer’ product in 62%yield.Subsequent stereoselective reduction of newly formed C=O with NaBH_4 produced title compound in 75%yield.X-ray diffraction analysis indicates the title compound adopts syn 1,2,3 stereochemistry and chair-chair conformation.The crystal structure is stabilized by hydrogen bonds.
The building block of N-alkyl derivative of allosamidin (chitinase inhibitor), 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride was stereoselectively synthesized in two steps under mild conditions. Nucleophilic addition of octylamine to 2-oxoglucopyranoside gave a’carbonyl group transfer ’product in 62% yield. Subsequent stereoselective reduction of newly formed C = O with NaBH_4 produced title compound in 75% yield. X-ray diffraction analysis indicates the title compound provisional syn 1, 2, 3 stereochemistry and chair -chair conformation.The crystal structure is stabilized by hydrogen bonds.