1396317-78-4

Basic information

• Product Name: (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate
• Synonyms: (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate
• CAS NO: 1396317-78-4
• Molecular Weight: 263.337
• Mol File: 1396317-78-4.mol

Chemical Properties

• CAS DataBase Reference: (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate(1396317-78-4)
• EPA Substance Registry System: (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate(1396317-78-4)

Safety Data

• Hazardous Substances Data: 1396317-78-4(Hazardous Substances Data)

Upstream product

• 10138-10-0 ethyl 4-oxobutanoate 
• 1396317-73-9 (S)-diethyl 4-(diallylamino)hept-2-ynedioate 
• 1428150-26-8 (S)-ethyl 4-(diallylamino)-5-oxopentanoate 
• 1428150-25-7 (S)-ethyl 4-(diallylamino)-5-hydroxypentanoate 
• 1428150-23-5 (S)-1-tert-butyl 5-ethyl-2-(diallylamino)pentanedioate 
• 91255-02-6 (S)-1-tert-butyl 5-ethyl 2-aminopentanedioate 
• 1119-33-1 (S)-2-Amino-pentanedioic acid 5-ethyl ester 
• 1396317-77-3 (S)-diethyl 4-(diallylamino)-(Z)-hept-2-enedioate 

Downstream Products

• 1396317-80-8 (2R,5S)-ethyl 5-(tert-butoxycarbonylamino)-2-hydroxycyclohex-3-enecarboxylate 
• 1396317-79-5 (5S)-ethyl 5-(diallylamino)-2-hydroxycyclohex-3-ene carboxylate 
• 1428150-18-8 (S)-diethyl 4-(bis(2-phenylallyl)amino)hept-2-ynedioate 
• 950690-19-4 ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate 

Relevant articles and documents

Chromatography-free synthesis of Corey's intermediate for Tamiflu

Column chromatography-free stereoselective synthesis of Corey's intermediate for Tamiflu (oseltamivir phosphate) was achieved, starting from l-glutamic acid γ-ethyl ester. The reagents and solvents used in the reaction scheme are industrially tractable, r

Compound, and a manufacturing method thereof, and manufacturing method of oseltamivir phosphate

PROBLEM TO BE SOLVED: To provide an intermediate useful in industrial production of oseltamivir phosphate which can inexpensively produce oseltamivir phosphate with a good optical yield; a production method thereof; and an oseltamivir phosphate production method using said production method.SOLUTION: The present invention provides a compound represented by the specified general formula (1). In the general formula (1), Rrepresents a hydrogen atom, or a protective group of a carboxyl group; Rand Reach independently represent a protective group of an amino group; and X represents a CORgroup (said Rrepresents a hydrogen atom, or a protective group of a carboxyl group), a hydroxymethyl group, or an aldehyde group.

COMPOUND AND METHOD FOR PRODUCING SAME, AS WELL AS METHOD FOR PRODUCING OSELTAMIVIR PHOSPHATE

A compound represented by the following general formula (1), and a method for producing the compound represented by the general formula (1), the method comprising: reacting together a compound represented by the following general formula (2), a compound represented by the following general formula (3), and a compound represented by the following general formula (4): HNR2R3 General Formula (3) wherein R1 represents any of a protective group of a carboxyl group, and a hydrogen atom, R2 and R3 each independently represent any of a protective group of an amino group, and a hydrogen atom, and R4 represents any of a protective group of a carboxyl group, and a hydrogen atom.

Two approaches toward the formal total synthesis of oseltamivir phosphate (Tamiflu): Catalytic enantioselective three-component reaction strategy and l-glutamic acid strategy

Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized l-glutamic acid γ-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to construct a six-membered ring core, after which manipulation of the functional groups and protecting groups accessed Corey's intermediate for the synthesis of oseltamivir phosphate. While the first synthesis was accomplished via four purification steps in 25.7% overall yield, albeit with moderate optical purity (76% ee), the second strategy achieved the synthesis via six purification steps in 19.8% overall yield with perfect enantiocontrol.