950690-19-4

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 
• 24424-99-5 di-tert-butyl dicarbonate 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 136994-78-0 ethyl (3aR,7R,7aS)-2,2-dimethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 138-59-0 shikimic acid 
• 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 
• 1428150-25-7 (S)-ethyl 4-(diallylamino)-5-hydroxypentanoate 
• 1428150-26-8 (S)-ethyl 4-(diallylamino)-5-oxopentanoate 
• 1396317-73-9 (S)-diethyl 4-(diallylamino)hept-2-ynedioate 
• 1396317-80-8 (2R,5S)-ethyl 5-(tert-butoxycarbonylamino)-2-hydroxycyclohex-3-enecarboxylate 

Downstream Products

• 891862-22-9 ethyl 3-acetamido-4-bromo-5-(tert-butoxycarbonylamino)cyclohex-1-ene-1-carboxylate 
• 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 

Relevant academic research and scientific papers

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.

Synthesis method of daphenanthrene key intermediate

The invention relates to a synthetic method of a Duffy key intermediate. The synthetic method comprises the following steps of by taking shikimic acid as a starting material and performing reactions including esterification reaction, selective oxidation a

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

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.

Formal synthesis of (-)-oseltamivir phosphate

The formal synthesis of (-)-oseltamivir phosphate (Tamiflutm) was accomplished starting from (S)-pyroglutamic acid. The synthesis comprised two carbon-carbon bond forming reactions, the first one being a diastereoselective, indium-mediated allylation of a pyroglutamic aldehyde derivative. However, attempts to effect the second carbon-carbon bond formation - cyclohexene ring closure - using an enol-exo aldolization of a dialdehyde resulted in the formation of a product with the opposite regioselectivity. This shortcoming could be overcome by using a reaction sequence of Mannich methylenation/ring-closing metathesis, which provided the desired regioisomer in high yield. Georg Thieme Verlag Stuttgart.New York.

Morita-Baylis-Hillman approach toward formal total synthesis of tamiflu and total synthesis of gabaculine

A Morita-Baylis-Hillman reaction mediated approach to the formal total synthesis of oseltamivir and the total synthesis of gabaculine is described. This strategy involves the enantiocontrolled preparation of Corey's intermediate in 22 % yield, which is pr

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.

An iron carbonyl approach to the influenza neuraminidase inhibitor oseltamivir

A novel synthetic route towards oseltamivir, an influenza neuraminidase inhibitor, has been achieved employing a cationic iron carbonyl complex, providing an alternate pathway with the potential to access diverse analogues. The Royal Society of Chemistry.

A short enantioselective pathway for the synthesis of the anti-influenza neuramidase inhibitor oseltamivir from 1,3-butadiene and acrylic acid

A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensiv