891831-22-4

Basic information

• Product Name: Carbamic acid, [(1S,5R,6R)-6-(acetylamino)-3-cyano-5-(1-ethylpropoxy)-3-cyclohexen- 1-yl]-, 1,1-dimethylethyl ester
• CAS NO: 891831-22-4
• Molecular Formula: C19H31N3O4
• Molecular Weight: 365.473
• Mol File: 891831-22-4.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,5R,6R)-6-(acetylamino)-3-cyano-5-(1-ethylpropoxy)-3-cyclohexen- 1-yl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,5R,6R)-6-(acetylamino)-3-cyano-5-(1-ethylpropoxy)-3-cyclohexen- 1-yl]-, 1,1-dimethylethyl ester(891831-22-4)
• EPA Substance Registry System: Carbamic acid, [(1S,5R,6R)-6-(acetylamino)-3-cyano-5-(1-ethylpropoxy)-3-cyclohexen- 1-yl]-, 1,1-dimethylethyl ester(891831-22-4)

Safety Data

• Hazardous Substances Data: 891831-22-4(Hazardous Substances Data)

Upstream product

• 891831-21-3 (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene 
• 108-24-7 acetic anhydride 
• 927395-72-0 tert-butyl [(1R,2S,6S)-7-acetyl-4-cyano-7-azabicyclo[4.1.0]hept-4-en-2-yl]carbamate 
• 584-02-1 2-pentanol 
• 927395-71-9 tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate 
• 891831-18-8 (6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester 
• 891831-16-6 (4R,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohexen-3-one 
• 891831-20-2 (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene 
• 891831-19-9 (3S,4R,5S)-5-(tert-butoxycarbonylamino)-3,4-(tert-butoxycarbonylimino)-1-cyanocyclohexene 
• 930275-47-1 (6-acetylamino-3-cyano-5-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester 
• 930275-48-2 (1S,2R)-2-(acetylamino)-1-(tert-butoxycarbonylamino)-4-cyclohexen-3-one 

Downstream Products

• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 

Relevant articles and documents

A PROCESS FOR THE PREPARATION OF INTERMEDIATE FOR THE PREPARATION OF OSELTAMIVIR PHOSPHATE

The present invention discloses an economic, simple, azide and azindine complexity free process for the synthesis of osletamivir phosphate (Tamiflu) by stereospecific amidoalkylation of imidazothiazolone from easily available L-cysteine via Ramberg- Backlund reaction and Sharpless-Reich protocol.

A concise synthesis of Tamiflu: third generation route via the Diels-Alder reaction and the Curtius rearrangement

Our third generation synthesis of Tamiflu was achieved in 12 steps from commercially available starting materials, using the Diels-Alder reaction and Curtius rearrangement as key steps.

Second generation catalytic asymmetric synthesis of tamiflu: Allylic substitution route

(Chemical Equation Presented) Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the C=C double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route.

De novo synthesis of tamiflu via a catalytic asymmetric ring-opening of meso-aziridines with TMSN3

An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality. Copyright