1149345-89-0

Basic information

• Product Name: ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate
• Synonyms: ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate
• CAS NO: 1149345-89-0
• Molecular Weight: 313.394
• Mol File: 1149345-89-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate(1149345-89-0)
• EPA Substance Registry System: ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate(1149345-89-0)

Safety Data

• Hazardous Substances Data: 1149345-89-0(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 1376576-18-9 ethyl (4R)-4-((2S,3R)-3-(hydroxymethyl)oxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 1376576-15-6 ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 1376576-12-3 ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-hydroxy-2-methylenebutanoate 
• 584-02-1 2-pentanol 
• 1350928-97-0 ethyl (1S,5R,6S)-7-acetyl-5-hydroxy-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1350928-96-9 ethyl (1S,5R,6S)-5-hydroxy-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1350928-95-8 ethyl (3S,4R,5R)-3-azido-4,5-dihydroxycyclohex-1-ene-1-carboxylate 
• 1350929-00-8 C₁₁H₁₄O₇S 
• 1350928-94-7 C₉H₁₂O₆S 
• 1350929-05-3 ethyl (3R,4R,5R)-4-acetamido-5-acetoxy-3-(1-ethylpropoxy)-cyclohex-1-ene-1-carboxylate 
• 1350929-04-2 ethyl (1S,5R,6S)-5-acetoxy-7-acetyl-7-azabicyclo[4,1,0]-hept-2-ene-3-carboxylate 
• 1350929-03-1 ethyl (1S,5R,6S)-5-acetoxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 
• 1350929-02-0 ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 

Downstream Products

• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 204255-06-1 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF OSELTAMIVIR AND METHYL 3-EPI-SHIKIMATE

The present invention discloses high yielding enantioselective process for synthesis of Oseltamivir from readily available starting material, cis-1,4-butene diol. The process features incorporation of chirality using sharpless asymmetric epoxidation (AE) and diastereoselective Barbier allylation and construction of cyclohexene carboxylic acid ester core through a ring closing metathesis (RCM) reaction. Further also disclosed herein is synthesis of (?)-methyl 3-epi-shikimate.

A new and efficient asymmetric synthesis of oseltamivir phosphate(Tamiflu) from D-mannose

Oseltamivir phosphate (Tamiflu) was synthesized from D-mannose through a short and practical synthetic route. A unique feature of the route is that the bulky 3-pentyloxy group and adjacent acetamide of Tamiflu were introduced at an early stage of the synthesis by copper-catalyzed regioselective ringopening of the 2,3-pentylidene ketal of D-lyxofuranoside. The D-lyxofuranoside ethylphosphonate precursor was then cyclized via an intramolecular Horner-Wadsworth-Emmons reaction to furnish the Tamiflu skeleton.

A new efficient synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid

New synthesis of oseltamivir phosphate was accomplished in 9 steps with a 27% overall yield from a readily available (-)-shikimic acid. Selective ring opening reaction of ketal and azide Mitsunobu reaction for facile replacement of a hydroxyl group by the N3 group at the C-3 position of (3R,4R,5R)-ethyl 4-hydroxy-5-(methoxymethoxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 4 and at the C-4 position of (3R,4S,5R)-ethyl 4-acetamido-5-hydroxy-3-(pentan-3-yloxy) cyclohex-1-enecarboxylate 7 successfully served as the key steps.