208394-55-2

Upstream product

• 300555-12-8 2,5-anhydro-4,6-O-benzylidene-3-O-p-toluenesulfonyl-L-idose 
• 208394-50-7 2,5-anhydro-4,6-isopropylidene-3-O-p-toluenesulfonyl-L-idose ethylene acetal 
• 208394-49-4 2,5-anhydro-3-O-p-toluenesulfonyl-L-idose ethylene acetal 
• 300555-11-7 2,5-anhydro-4,6-O-benzylidene-3-O-methanesulfonyl-L-idose 
• 300555-13-9 2,5-anhydro-4,6-O-benzylidene-3-deoxy-L-threo-hex-2-enose ethylene acetal 
• 218449-02-6 2,5-anhydro-3-O-methanesulfonyl-L-idose ethylene acetal 
• 208394-52-9 2,5-anhydro-3-deoxy-4,6-O-benzylidene-L-xylo-hexose ethylene acetal 
• 98-59-9 p-toluenesulfonyl chloride 
• 208394-54-1 2,5-anhydro-3-deoxy-L-xylo-hexose ethylene acetal 
• 300555-14-0 2,5-anhydro-4,6-O-benzylidene-3-deoxy-L-xylo-hexose ethylene acetal 

Downstream Products

• 129064-92-2 2,5-anhydro-4-O-benzoyl-1-iodo-1,3,6-trideoxy-L-ribo-hexitol 
• 24570-49-8 (+)-muscarine iodide 
• 112020-37-8 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-ribo-hexitol 
• 111967-30-7 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-xylo-hexitol 
• 300555-15-1 Benzoic acid (2S,3R,5S)-5-formyl-2-methyl-tetrahydro-furan-3-yl ester 
• 218449-15-1 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-ribo-hexose ethylene acetal 
• 218449-12-8 2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal 
• 208398-79-2 Benzoic acid (2S,3S,5S)-5-formyl-2-methyl-tetrahydro-furan-3-yl ester 
• 208401-63-2 2,5-anhydro-4-O-benzoyl-1-iodo-1,3,6-trideoxy-L-xylo-hexitol 
• 208394-57-4 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-xylo-hexose ethylene acetal 

Relevant academic research and scientific papers

Stereospecific synthesis of (+)-muscarine from D-glucose, suitable for preparation of 5-substituted analogues

A stereospecific synthesis of (+)-muscarine iodide (1) has been achieved starting from D-glucose as a chiral precursor. The key steps of the synthesis involved a stereospecific cyclization of 3,5-di-O-mesyl derivative 3 into the 2,5-anhydride 4, the stereospecific catalytic hydrogenation of unsaturated derivative 6, and the C-4 epimerization of alcohol 12 by Mitsunobu reaction.

A divergent synthesis of (+)-muscarine and (+)-epi-muscarine from D-glucose

A novel stereospecific synthesis of (+)-muscarine and (+)-epi-muscarine has been achieved by utilizing D-glucose as a chiral precursor. The key steps of the synthesis involved stereospecific cyclization of 3,5-di-O-sulfonyl-D-glucofuranose derivatives into the corresponding 2,5-anhydrides, and stereospecific hydrogenation of 2,5-anhydro-L-threo-hex-2-enose ethylene acetal derivatives, thus providing an access to divergent intermediates for the preparation of both target molecules in a fully stereospecific manner. (C) 2000 Elsevier Science Ltd.