24570-49-8

Usage

Uses

A cholinergic receptor involved in the production of gastric acid

Upstream product

• 103664-41-1 (-)-(2S,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran 
• 124-40-3 dimethyl amine 
• 74-88-4 methyl iodide 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 75499-91-1 2,5-anhydro-1,4-dideoxy-6-O-(p-tolylsulphonyl)-D-ribo-hexitol 
• 115352-39-1 (2R)-1-benzyloxy-2-hydroxy-pent-4-yne 
• 476315-81-8 (2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 75499-86-4 (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol 
• 501-38-2 (-)-normuscarine 
• 129064-90-0 (2S,5S)-5-Iodomethyl-2-methyl-dihydro-furan-3-one 
• 102735-38-6 (2S,4S,5S)-2-Iodomethyl-5-methyl-tetrahydrofuran-4-ol 
• 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 

Downstream Products

• 2303-35-7 (+)-muscarine chloride 
• 104487-60-7 L-(+)-muscarine tetraphenylborate 

Relevant academic research and scientific papers

A concise asymmetric synthesis of (+)-muscarine from (S)-γ-hydroxymethyl-γ-butyrolactone

A highly stereoselective synthesis of (+)-muscarine iodide has been achieved in eight steps and 20% overall yield from commercially available (S)-γ-hydroxymethyl-γ-butyrolactone.

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 of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2(5H)-furanone

(+)-Muscarine has been synthesized from (S)-(-)-5-hydroxy-2(5H)-furanone via rather a long pathway to provide easy access to a wide variety of its analogues. (C) 2000 Published by Elsevier Science Ltd.

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.

A Concise Enantioselective Synthesis of (+)-Muscarine from (R)-O-Benzylglycidol

A concise enantioselective synthesis of (+)-muscarine has been established via the novel formation of a 3,4-dihydrofuran starting from (R)-O-benzylglycidol.