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
Source: 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
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

3
checked on Feb 22, 2018

WEB OF SCIENCETM
Citations

4
checked on Jan 29, 2018

Page view(s)

20
checked on Feb 19, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.