17812-38-3

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-6β-(3-Furyl)-α,α,3α-trimethylpiperidine-2β-(1-propanol) is used as a potential pharmaceutical agent for its unique structural features. The combination of the furan and 1-propanol groups, along with the methyl groups, may contribute to its interaction with biological targets, offering possible applications in the development of new drugs.
Used in Industrial Applications:
In the industrial sector, (2S)-6β-(3-Furyl)-α,α,3α-trimethylpiperidine-2β-(1-propanol) may serve as a building block or intermediate in the synthesis of various chemical products. Its specific structural elements could be leveraged to create novel materials or compounds with tailored properties for specialized uses.

Upstream product

• 129866-39-3 {(2R,3R)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyl]-2-methyl-oxiranyl}-methanol 
• 53913-09-0 6-furan-3-yl-3-methyl-2-(3-methyl-but-3-enyl)-piperidine 
• 53913-09-0 6-furan-3-yl-3-methyl-2-(3-methyl-but-3-enyl)-piperidine 
• 229170-63-2 (-)-(2R,3R,6S)-(E)-N-benzyloxycarbonyl-2-(2-ethoxycarbonyl-1-ethenyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine 
• 229170-64-3 (-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine 
• 229170-62-1 (-)-(2R,3R,6S)-N-benzyloxycarbonyl-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine 
• 229170-57-4 (-)-(2S,5R,6R)-2-(3-furyl)-3-methyl-1-aza-8-oxabicyclo[4.3.0]nonan-9-one 
• 209160-33-8 (+)-(2S,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[4.3.0]nonane 
• 229170-65-4 (-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine 
• 137172-50-0 (4aS,5R,8S)-8-Furan-3-yl-2,2,5-trimethyl-octahydro-pyrido[1,2-b][1,2]oxazine 
• 137105-77-2 4-((2S,3R,6S)-1-Benzyl-6-furan-3-yl-3-methyl-piperidin-2-yl)-2-methyl-butan-2-ol 
• 917-64-6 methyl magnesium iodide 
• 32598-78-0 (2S)-1-formyl-6c-furan-3-yl-3t-methyl-2r-(3-oxo-butyl)-piperidine 

Downstream Products

• 4849-88-1 (-)-Anhydronupharamin 

Relevant academic research and scientific papers

A short and enantiospecific synthesis of (-)-nupharamine

A short and convergent synthesis of the naturally occurring sesquiterpenoid piperidine alkaloid (-)-nupharamine is presented starting from (-)-isopinocampheol via cross metathesis and reductive amination as the key steps. Georg Thieme Verlag Stuttgart.

Stereoselective total synthesis of (-)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C-C bond formation

An efficient stereoselective synthesis of the nuphar alkaloid, (-)-nupharamine, is reported. The key features include the Lewis acid catalyzed reaction of an α-chlorosulfide with a silyl ketene acetal for C-C bond formation, creation of the stereocenter at C2 by a diastereoselective reaction of allyl indium with a sulfinimine and reductive amination for the introduction of the C6 stereocenter of the piperidine ring.

Synthesis of two nuphar alkaloids by allenic hydroxylamine cyclisation

A highly diastereoselective silver-catalysed cyclisation of a 2-substituted β-allenic hydroxylamine is reported. The resulting trans-isoxazolidine is converted into two Nuphar alkaloids by a sequence involving cross-metathesis and intramolecular reductive amination. Georg Thieme Verlag Stuttgart - New York.

Total synthesis of (-)-nupharamine and (+)-3-epinupharamine via asymmetric nitroso Diels-Alder reaction

Chiral synthesis of (-)-nupharamine and (+)-3-epinupharamine, based on elaboration of the intramolecular asymmetric Diels-Alder reaction of N-acylnitroso compounds and the introduction of the furyl group in a fully stereocontrolled manner, is described.

Chiral Synthesis of (-)-Nupharamine

Reaction of the optically active alkenyloxirane with formic acid in the presence of palladium(0)-phosphine catalyst gave the homoallylic alcohol selectively, which was converted to (-)-nupharamine.