950690-19-4

Basic information

• Product Name: ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate
• Synonyms: ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate
• CAS NO: 950690-19-4
• Molecular Weight: 267.325
• Mol File: 950690-19-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate(950690-19-4)
• EPA Substance Registry System: ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate(950690-19-4)

Safety Data

• Hazardous Substances Data: 950690-19-4(Hazardous Substances Data)

Upstream product

• 891862-20-7 tert-butyl 4-bromo-7-oxo-6-azabicyclo[3.2.1]oct-2-ene-6-carboxylate 
• 64-17-5 ethanol 
• 1428733-27-0 tert-butyl (3aS,7aR)-5-formyl-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate 
• 1428733-26-9 tert-butyl (4S,5R)-5-allyl-4-(2-formylallyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1428733-23-6 tert-butyl (4S,5R)-5-allyl-2,2-dimethyl-4-(3-oxopropyl)oxazolidine-3-carboxylate 
• 1428733-22-5 tert-butyl (4S,5R)-5-allyl-4-(3-hydroxypropyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1428733-21-4 tert-butyl (4S,5R)-1,5-dihydroxyoct-7-en-4-ylcarbamate 
• 1428733-20-3 tert-butyl (S)-2-[(R)-1-hydroxybut-3-enyl]-5-oxopyrrolidine-1-carboxylate 
• 1428733-30-5 (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylic acid 
• 1428733-25-8 tert-butyl (4S,5R)-2,2-dimethyl-5-(2-oxoethyl)-4-(3-oxopropyl)oxazolidine-3-carboxylate 
• 185303-87-1 tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate 
• 1298023-90-1 (5S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-one-5-carbothioic acid ethyl ester 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 1428733-31-6 ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 

Downstream Products

• 90242-16-3 (5S)-5-<(tert-butoxycarbonyl)amino>cyclohexadienecarboxylic acid 
• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 950690-28-5 ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-[(methylsulfonyl)oxy]-cyclohexa-1-ene-1-carboxylate 
• 950690-25-2 (3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate 
• 891862-22-9 ethyl 3-acetamido-4-bromo-5-(tert-butoxycarbonylamino)cyclohex-1-ene-1-carboxylate 

Relevant articles and documents

Rapid Enantioselective and Diastereoconvergent Hybrid Organic/Biocatalytic Entry into the Oseltamivir Core

A formal synthesis of the antiviral drug (-)-oseltamivir (Tamiflu) has been accomplished starting from m-anisic acid via a dissolving metal or electrochemical Birch reduction. The correct absolute stereochemistry is efficiently set through enzyme-catalyzed carbonyl reduction on the resultant racemic α,β-unsaturated ketone. A screen of a broad ketoreductase (KRED) library identified several that deliver the desired allylic alcohol with nearly perfect facial selectivity at the new center for each antipodal substrate, indicating that the enzyme also is able to completely override inherent diastereomeric bias in the substrate. Conversion is complete, with d-glucose serving as the terminal hydride donor (glucose dehydrogenase). For each resulting diastereomeric secondary alcohol, O/N-interconversion is then efficiently effected either by synfacial [3,3]-sigmatropic allylic imidate rearrangement or by direct, stereoinverting N-Mitsunobu chemistry. Both stereochemical outcomes have been confirmed crystallographically. The α,β-unsaturation is then introduced via an α-phenylselenylation/oxidation/pyrolysis sequence to yield the targeted (S)-N-acyl-protected 5-amino-1,3-cyclohexadiene carboxylates, key advanced intermediates for oseltamivir pioneered by Corey (N-Boc) and Trost (N-phthalamido), respectively.

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.

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