1062100-87-1

Basic information

• Product Name: diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate
• Synonyms: diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate
• CAS NO: 1062100-87-1
• Molecular Weight: 476.55
• Mol File: 1062100-87-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate(1062100-87-1)
• EPA Substance Registry System: diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate(1062100-87-1)

Safety Data

• Hazardous Substances Data: 1062100-87-1(Hazardous Substances Data)

Upstream product

• 1062100-84-8 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-bromocyclohexene 
• 762-04-9 phosphonic acid diethyl ester 
• 196618-13-0 oseltamivir 
• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 764639-63-6 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1373702-86-3 C₂₃H₃₅N₃O₆S₂ 

Downstream Products

• 949962-56-5 (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid 
• 1122748-00-8 C₁₅H₂₉N₂O₅P 
• 1122748-01-9 C₁₆H₃₁N₄O₅P 
• 1401808-94-3 C₁₈H₃₅N₄O₅P 
• 950478-34-9 diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 

Relevant articles and documents

A short synthetic pathway via three-component coupling reaction to tamiphosphor possessing anti-influenza activity

Three-component coupling reaction of (pent-3-oxy)acetaldehyde, (Z)-N-(2-nitrovinyl)acetamide, and tetraethyl 1,1-diylbis(phosphonate) is performed in a one-pot operation, followed by reduction of the nitro group and hydrolysis of the phosphonate ester, to afford 8.7% overall yield of tamiphosphor as a potent neuraminidase inhibitor with IC50 and EC50 values of 2.5 and 31.5 nM against wild-type H1N1 influenza virus. The tamiphosphor (5R)-epimer is a less active anti-influenza agent with IC50 and EC50 values of 39 and 117 nM.

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).