Please use this identifier to cite or link to this item: https://doi.org/10.1016/0008-6215(92)80042-Y
Title: Synthesis, reactions, and crystal structure of 5-azido-6-O-benzoyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-gluc ofuranose
Authors: Lee, C.-K. 
Jiang, H. 
Koh, L.L. 
Issue Date: 1-Jan-1992
Citation: Lee, C.-K., Jiang, H., Koh, L.L. (1992-01-01). Synthesis, reactions, and crystal structure of 5-azido-6-O-benzoyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-gluc ofuranose. Carbohydrate Research 225 (1) : 99-111. ScholarBank@NUS Repository. https://doi.org/10.1016/0008-6215(92)80042-Y
Abstract: 5-Bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-t alofuranose (7) was obtained by treatment of 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D -glucofuranose (3) with N-bromosuccinimide followed by Zemplen O-deacylation and an oxidation-reduction sequence. Nucleophilic displacement of the bromide in 7 with potassium azide readily gave the corresponding 5-azido-5-deoxy-allo derivative 8. Treatment of the 3-trifluoromethanesulphonate of 8 with tris(dimethylamino)sulphonium difluorotrimethylsilicate gave 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropy lidene-α-D-glucofuranose (17). The configuration at C-3 in 17 was confirmed by X-ray crystallography of the 6-benzoate 19.
Source Title: Carbohydrate Research
URI: http://scholarbank.nus.edu.sg/handle/10635/77197
ISSN: 00086215
DOI: 10.1016/0008-6215(92)80042-Y
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