177341-35-4

Upstream product

• 26784-23-6 cis,cis-2,6-bis(methoxycarbonyl)-4-hydroxypiperidine 
• 138-60-3 chelidamic acid 
• 107-30-2 chloromethyl methyl ether 
• 177341-34-3 (2S,4S,6R)-4-Hydroxy-piperidine-1,2,6-tricarboxylic acid benzyl ester dimethyl ester 

Downstream Products

• 177341-44-5 (2R,4R,6S)-2-Acetoxymethyl-6-methanesulfonyloxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester 
• 177341-40-1 (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine 
• 224647-18-1 (2R,4S,6S)-2,6-Bis-acetoxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester 
• 177341-65-0 (2R,4S,6S)-2-Acetoxymethyl-6-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester 
• 177341-49-0 (2R,4S,6R)-1-Benzyl-4-methoxymethoxy-6-methyl-piperidine-2-carbaldehyde 
• 177341-48-9 ((2R,4S,6R)-1-Benzyl-4-methoxymethoxy-6-methyl-piperidin-2-yl)-methanol 
• 177473-33-5 (2R,6R)-1-Benzyl-6-methyl-piperidine-2-carbaldehyde 
• 177473-32-4 ((2R,6R)-1-Benzyl-6-methyl-piperidin-2-yl)-methanol 
• 177341-36-5 (2R,4S,6S)-2,6-Bis-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D

Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase (ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee ≥ 98%). The general method is used to effect the synthesis of (±)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.