引用本文:
Fu Yi Zhang, Chun Li Wu, Cui Zhang, Hong Min Liu. Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride[J]. Chinese Chemical Letters,
2010, 21(7): 798-801.
doi:
10.1016/j.cclet.2010.02.020
Citation: Fu Yi Zhang, Chun Li Wu, Cui Zhang, Hong Min Liu. Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride[J]. Chinese Chemical Letters, 2010, 21(7): 798-801. doi: 10.1016/j.cclet.2010.02.020
Citation: Fu Yi Zhang, Chun Li Wu, Cui Zhang, Hong Min Liu. Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride[J]. Chinese Chemical Letters, 2010, 21(7): 798-801. doi: 10.1016/j.cclet.2010.02.020
Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride
摘要:
The building block of N-alkyl derivative of allosamidin (chitinase inhibitor), 4,6-O-benzylidene-N-octyl-D-allosamine hydro-chloride 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 NaBH4 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.
English
Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride
Abstract:
The building block of N-alkyl derivative of allosamidin (chitinase inhibitor), 4,6-O-benzylidene-N-octyl-D-allosamine hydro-chloride 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 NaBH4 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.
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