1062100-77-9

Basic information

• Product Name: (1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate
• Synonyms: (1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate
• CAS NO: 1062100-77-9
• Molecular Weight: 441.16
• Mol File: 1062100-77-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate(1062100-77-9)
• EPA Substance Registry System: (1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate(1062100-77-9)

Safety Data

• Hazardous Substances Data: 1062100-77-9(Hazardous Substances Data)

Upstream product

• 1056467-86-7 (3aS,4S,5S,7aS)-8-acetyl-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-4,5-epimino-1,3-benzodioxole 
• 1106677-14-8 N-[(3aR,4R,5S,7aS)-4,7-dibromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]acetamide 
• 1062100-76-8 N-[(1R,2R,5S,6S)-4-bromo-2-(1-ethoxypropoxy)-5,6-dihydroxycyclohex-3-en-1-yl]acetamide 
• 40635-67-4 acetoxyisobutyryl bromide 

Downstream Products

• 1122581-40-1 N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide 
• 1122748-00-8 C₁₅H₂₉N₂O₅P 
• 1401808-94-3 C₁₈H₃₅N₄O₅P 
• 949962-57-6 (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid 
• 1122748-01-9 C₁₆H₃₁N₄O₅P 

Relevant articles and documents

Development of oseltamivir phosphonate congeners as anti-influenza agents

Oseltamivir phosphonic acid (tamiphosphor, 3a), its monoethyl ester (3c), guanidino-tamiphosphor (4a), and its monoethyl ester (4c) are potent inhibitors of influenza neuraminidases. They inhibit the replication of influenza viruses, including the oseltamivir-resistant H275Y strain, at low nanomolar to picomolar levels, and significantly protect mice from infection with lethal doses of influenza viruses when orally administered with 1 mg/kg or higher doses. These compounds are stable in simulated gastric fluid, liver microsomes, and human blood and are largely free from binding to plasma proteins. Pharmacokinetic properties of these inhibitors are thoroughly studied in dogs, rats, and mice. The absolute oral bioavailability of these compounds was lower than 12%. No conversion of monoester 4c to phosphonic acid 4a was observed in rats after intravenous administration, but partial conversion of 4c was observed with oral administration. Advanced formulation may be investigated to develop these new anti-influenza agents for better therapeutic use.

A concise and flexible synthesis of the potent anti-influenza agents tamiflu and tamiphosphor

(Chemical Equation Presented) Tamiflu and the highly potent neuraminidase inhibitor tamiphosphor have been synthesized in 11 steps and greater than 20% overall yields from an haloarene (1S,2S)-cis-diol. The key transformations include a regio- and stereoselective bromoamidation, and a palladium-catalyzed carbonylation or phosphonylation reaction (see scheme; tamiflu: A = CO 2Et, B = NH3+H2PO4 -, tamiphosphor: A = PO(ONH4)2, B = NH 2).