Please use this identifier to cite or link to this item:
Title: Synthesis and reactions of 3-C-branched-chain analogues of 3,6-anhydrodeoxynojirimycin
Authors: Lee, C.K.
Jiang, H. 
Scofield, A.M.
Issue Date: 1997
Citation: Lee, C.K.,Jiang, H.,Scofield, A.M. (1997). Synthesis and reactions of 3-C-branched-chain analogues of 3,6-anhydrodeoxynojirimycin. Journal of Carbohydrate Chemistry 16 (1) : 49-62. ScholarBank@NUS Repository.
Abstract: The syntheses of 3,6-anhydro-1-deoxy-3-C-ethoxycarbonylmethyl- (4) and 3-C-(2-hydroxyethyl)nojirimycin (5) from 5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D- glucofuranose (8) are described. The key intermediate is 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2- O-isopropylidene-α-D-ribo-hex-3-enofuranose (11) which was obtained by condensation of 5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo- hexos-3-ulofuranose (10) with (ethoxycarbonylmethylene)triphenylphosphorane. Conventional benzoylation of 4 resulted in the formation of the lactones 13a and 13b. The 3-C-(2-hydroxyethyl) analogue (5) was synthesized by lithium aluminum hydride reduction of 3,6-anhydro-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl-1,2-O-isopropylidene- α-D-glucofuranose (12), followed by deacetalation, and hydrogenation.
Source Title: Journal of Carbohydrate Chemistry
ISSN: 07328303
Appears in Collections:Staff Publications

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

Page view(s)

checked on Sep 22, 2022

Google ScholarTM


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