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 shu

Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride

a Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450052, China;
b School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, China

Received Date: 9 November 2009

Fund Project: The authors are grateful for the financial supports from the National Natural Science Foundation of China (No. 20972142) and the State Key Laboratory of Bio-organic and Natural Products Chemistry, CAS (No. 08417).

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.
- 2-Oxoglucopyranoside,
- 4,6-O-benzyttdene-N-octyl-D-allosamine hydrochloride,
- X-ray structure
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