129064-92-2

Upstream product

• 102735-38-6 (2S,4S,5S)-2-Iodomethyl-5-methyl-tetrahydrofuran-4-ol 
• 65-85-0 benzoic acid 
• 300555-12-8 2,5-anhydro-4,6-O-benzylidene-3-O-p-toluenesulfonyl-L-idose 
• 129064-90-0 (2S,5S)-5-Iodomethyl-2-methyl-dihydro-furan-3-one 
• 129064-86-4 Methanesulfonic acid 4,4-dimethoxy-5-methyl-tetrahydro-furan-2-ylmethyl ester 
• 129064-88-6 Methanesulfonic acid 5-methyl-4-oxo-tetrahydro-furan-2-ylmethyl ester 
• 90647-90-8 4,4-dimethoxy-5-methyl-tetrahydro-furan-2-carboxylic acid methyl ester 
• 98272-76-5 5-methyl-4-oxo-tetrahydro-furan-2-carboxylic acid methyl ester 
• 15358-07-3 (+/-)-2-Methyl-3,3-dimethoxy-5-hydroxy-methyl-tetrahydrofuran 
• 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 
• 208394-55-2 2,5-anhydro-3-deoxy-6-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal 
• 218449-12-8 2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal 

Downstream Products

• 24570-49-8 (+)-muscarine iodide 
• 326805-91-8 (-)-(2S,4R,5S)-2-[(Dimethylamino)methyl]-4-benzyloxy-5-methyltetrahydrofuran 
• 326805-89-4 (-)-(2S,4R,5S)-2-(Iodomethyl)-4-benzyloxy-5-methyltetrahydrofuran 

Relevant academic research and scientific papers

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.

Synthesis and pharmacological characterization of new chiral derivatives of muscarine and allo-muscarine

Novel derivatives of natural muscarine and allo-muscarine, i.e. the benzyl ethers (-)-10 and (-)-12 and the benzoate (-)-13, were synthesized in very high enantiomeric excess. Target compounds were tested in vitro on guinea pig tissues, and their muscarin

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.

Chemoenymatic Synthesis of the Eight Stereoisomeric Muscarines

Efficient synthesis of the eight stereoisomers of muscarine have been accomplished by dehydrogenase-catalyzed reduction of iodo ketones (+/-)-3a and (+/-)-3b. 3α,20β-Hydroxysteroid dehydrogenase from Streptomyces hydrogenans exhibited high enantiomeric and diastereotopic selectivity for (+/-)-3a, yielding an equimolar mixture of iodo alcohol (-)-4 (2S,4S,5S) (96percent ee) and iodo ketone (+)-3a (2R,5R) (96percent ee) which was reduced by sodium borohydride to a mixture of (+)-4 and (+)-5. 3β,17β-Hydroxysteroid dehydrogenase from Pseudomonas testosteroni reduced (+/-)-3b wih high diasterotopic selectivity to give an equimolar mixture of iodo alcohols (+)-6 (2R,4S,6S) (>99percent ee) and (-)-7 (2S,4S,5R) (81percent ee).Synthesis of the remaining iodo alcohols was achieved by applying the Mitsunobo procedure to (-)-4, (-)-7, and (+)-6.The enantiomeric excess of intermediates 4-7 was determined by HPLC analysis of the (R)-(+)-MTPA esters.The chiral iodo alcohols 4-7 were then transformed into the final derivatives by conventional chemical manipulations.