817196-16-0

Upstream product

• 817196-20-6 2,2-dimethyl-propionic acid 1-benzyl-3-hydroxy-piperidin-2-ylmethyl ester 
• 27230-48-4 3-hydroxy-2-hydroxymethylpiperidine 
• 14047-53-1 3-hydroxy-2-hydroxymethylpyridine 
• 531504-63-9 2-hydroxymethyl-piperidin-3-ol; hydrochloride 
• 14173-30-9 3-hydroxy-2-hydroxymethylpyridine hydrochloride 
• 100-39-0 benzyl bromide 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 1378532-38-7 (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate 
• 1378532-39-8 (2S,3R)-1-(phenylmethyl)-2-{[(2S)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αS)-α-methoxy-α-(trifluoromethyl)benzeneacetate 
• 1378532-31-0 (+)-(2R,3R)-[3-(acetyloxy)-1-(phenylmethyl)piperidin-2-yl]methyl 2,2-dimethylpropanoate 
• 1378532-35-4 (-)-(2R,3R)-1-benzyl-3-hydroxypiperidine-2-methanol 
• 1378532-40-1 C₃₃H₃₃F₆NO₆ 
• 1378532-41-2 C₃₃H₃₃F₆NO₆ 
• 1378532-32-1 (-)-(2S,3S)-[3-(acetyloxy)-1-(phenylmethyl)piperidin-2-yl]methyl 2,2-dimethylpropanoate 
• 1378532-34-3 (+)-(2S,3S)-1-benzyl-3-hydroxypiperidine-2-methanol 
• 1378532-42-3 (2S,3S)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate 
• 1378532-43-4 (2S,3S)-1-(phenylmethyl)-2-{[(2S)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αS)-α-methoxy-α-(trifluoromethyl)benzeneacetate 
• 1378532-51-4 (-)-(1S,3R,6R)-7-benzyl-3-fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-oxide 
• 1378532-47-8 (-)-(2S,4aR,8aS)-2-fluorohexahydro-5-(phenylmethyl)-4H-1,3,2-dioxaphosphorino[5,4-b]pyridine 2-oxide 
• 1378532-54-7 (+)-(1S,3R,6S)-7-benzyl-3-fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-oxide 
• 1378532-52-5 (+)-(1S,3S,6S)-7-benzyl-3-fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-oxide 

Relevant academic research and scientific papers

Synthesis and characterization of enantiomerically pure cis- and trans-3-fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-oxides as acetylcholine mimetics and inhibitors of acetylcholinesterase

The title compounds, the P(3)-axially and P(3)-equatorially substituted cis- and trans-configured 7-benzyl-3-fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-oxides (=7-benzyl-3-fluoro-2,4-dioxa-7-aza-3-phosphabicyclo[4.4.0]decane 3-oxides=5-benzyl-2-fluorohexahydro-4H-1,3,2-dioxaphosphorino[5,4-b]pyridine 2-oxides) were prepared (ee>99%) and fully characterized (Schemes 2 and 4). The absolute configurations were established from that of their precursors, the enantiomerically pure cis- and trans-1-benzyl-3-hydroxypiperidine-2-methanols which were unambiguously assigned. Being configuratively fixed and conformationally constrained phosphorus analogues of acetylcholine, they mimic rotamers of acetylcholine and are suitable probes for the investigation of molecular interactions with acetylcholinesterase. As determined by kinetic methods, the compounds are irreversible inhibitors of the enzyme displaying significant stereoselectivity. Copyright

2,4-Dioxa-7-aza-, 2,4-dioxa-8-aza-, and 2,4-dioxa-9-aza-3-phosphadecalins as rigid acetylcholine mimetics: Syntheses and characterization

Phosphorylation of suitable piperidine precursors yielded a series of novel decalin-type O,N,P-heterocycles. The title compounds, P(3)-axially and P(3)-equatorially X-substituted, cis- and trans-configurated 2,4-dioxa-7-aza-, 2,4-dioxa-8-aza-, and 2,4-dioxa-9-aza-3-phosphabicyclo[4.4.0]decane 3-oxides (X = Cl, F, 4-nitrophenoxy, and 2,4-dinitrophenoxy), are configuratively fixed and conformationally constrained P-analogues of acetylcholine and as such represent acetylcholine (7-aza and 9-aza isomers) or γ-homo-acetylcholine mimetics (8-aza isomers). Being irreversible inhibitors of acetylcholinesterase (AChE), the compounds are considered to be suitable probes for the investigation of the stereochemical course of the inhibition reaction by 31P-NMR spectroscopy. Moreover, the design of these mimetics will enable studies of molecular interactions with AChE, in particular, the recognition conformation of acetylcholine.