35119-35-8

Upstream product

• 116246-31-2 (2R,3S,5S)-5-Aminomethyl-2-methyl-tetrahydro-furan-3-ol 
• 74-88-4 methyl iodide 
• 116246-29-8 (2R,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbonitrile 
• 2209-02-1 (+/-)-muscarine iodide 
• 116246-31-2 (2S,3R,5S)-5-Aminomethyl-2-methyl-tetrahydro-furan-3-ol 
• 2209-19-0 (2S,4R,5S)-4-Hydroxy-5-methyl-tetrahydro-furan-2-carboxylic acid dimethylamide 
• 74282-54-5 (3R,5S,6S)-3,5-Bis-benzyloxymethoxy-6-methyl-tetrahydro-pyran-2-ol 
• 74282-55-6 (3S,5R,6R)-3,5-Bis-benzyloxymethoxy-6-methyl-tetrahydro-pyran-2-one 
• 74282-56-7 (2R,4S,5S)-2,4-Bis-benzyloxymethoxy-5-hydroxy-hexanoic acid dimethylamide 
• 74282-57-8 Methanesulfonic acid (1R,2R,4S)-2,4-bis-benzyloxymethoxy-4-dimethylcarbamoyl-1-methyl-butyl ester 
• 501-37-1 (+/-)-normuscarine 
• 116246-29-8 (2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbonitrile 
• 104048-27-3 (+/-)-epiallo-muscarine iodide 
• 2209-19-0 2-Methyl-3-hydroxy-tetrahydrofuran-carbonsaeure-⁽⁵⁾-dimethylamid 

Downstream Products

• 108192-52-5 (+/-)-allomuscarone; tetraphenyl borate 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF THE MUSCARINES

The total syntheses of racemic muscarine and allo-muscarine have been achieved using as a key step the stereospecific photochemical ring expansion of a cyclobutanone.

Chelation-Controlled Synthesis of (+/-)-Muscarine

The chelation controlled addition of Grignard reagents to chiral α-alkoxy aldehydes to give threo diol derivatives is synthetically useful in highly oxygenated systems and is used here as the key step in a novel synthesis of (+/-)-muscarine from cyclopentadiene.