1427281-83-1

Basic information

• Product Name: (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate
• Synonyms: (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate
• CAS NO: 1427281-83-1
• Molecular Weight: 459.629
• Mol File: 1427281-83-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate(1427281-83-1)
• EPA Substance Registry System: (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate(1427281-83-1)

Safety Data

• Hazardous Substances Data: 1427281-83-1(Hazardous Substances Data)

Upstream product

• 54125-02-9 danishefsky's diene 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 

Downstream Products

• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 1427281-91-1 (-)-(2S,4R)-2-(hydroxymethyl)-1-[(1S)-1-phenylethyl]piperidin-4-ol 
• 65253-04-5 (-)-8-phenylmenthol 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 1431164-77-0 (-)-(1R,2S,5R)-8-phenylmenthyl (2R)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1427281-87-5 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate 

Relevant articles and documents

Highly stereoselective cycloadditions of Danishefsky's diene to (-)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels-Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl. Adducts were formed in good yields (78-81%), with complete regioselectivity and high diastereoselectivity (87-96%). The absolute configuration of the adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. These cycloadducts can serve as precursors for bioactive piperidinic azasugars and pipecolic acid derivatives.