129064-93-3

Upstream product

• 102735-37-5 (2S,3S,5R)-5-Iodomethyl-2-methyl-tetrahydro-furan-3-ol 
• 65-85-0 benzoic acid 
• 171036-33-2 Benzoic acid (2S,3R,5R)-5-hydroxymethyl-2-methyl-tetrahydro-furan-3-yl ester 
• 582-25-2 Potassium benzoate 
• 15358-07-3 (+/-)-2-Methyl-3,3-dimethoxy-5-hydroxy-methyl-tetrahydrofuran 
• 98272-76-5 5-methyl-4-oxo-tetrahydro-furan-2-carboxylic acid methyl ester 
• 129064-91-1 (2R,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 
• 153974-06-2 2,5-anhydro-3,4,6-tri-O-methanesulfonyl-L-idose ethylene acetal 
• 181645-44-3 Methanesulfonic acid (2S,3S,5R)-5-[1,3]dioxolan-2-yl-2-methyl-tetrahydro-furan-3-yl ester 
• 153974-01-7 2,5-anhydro-3,6-di-O-methanesulfonyl-L-idose ethylene acetal 
• 181645-42-1 2,5-anhydro-3,6-di-O-methanesulfonyl-4-O-p-toluenesulfonyl-L-idose ethylene acetal 

Downstream Products

• 326805-92-9 (-)-(2R,4R,5S)-2-[(Dimethylamino)methyl]-4-benzyloxy-5-methyltetrahydrofuran 
• 326805-90-7 (-)-(2R,4R,5S)-2-(Iodomethyl)-4-benzyloxy-5-methyltetrahydrofuran 

Relevant academic research and scientific papers

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

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.