Stereoselective synthesis of the thermodynamically less stable manno isomers from a nitro sugar |
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| Authors: | Tuhru Sakakibara Rokuro Sudoh |
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| Affiliation: | Department of Chemistry, Faculty of Science, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo l52 Japan |
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| Abstract: | Reaction of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-o--D-erythro-hex-2-enopyranoside (2) with hydrazoic acid, hydrogen cyanide, theophylline, and 2,6-dichloropurine under weakly acidic or neutral conditions resulted in the stereo-selective formation of addition products having the thermodynamically less-stable manno configuration, whereas reaction of 2 with more-basic reagents yielded mainly products having the more stable gluco configuration. |
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