Ethyl (1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate

Base Information

• Chemical Name: Ethyl (1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate
• CAS No.: 204254-96-6
• Molecular Formula: C14H22O4
• Molecular Weight: 254.326
• European Community (EC) Number: 429-020-1,606-550-3
• UNII: 6T6E34US7J
• DSSTox Substance ID: DTXSID50942603
• Nikkaji Number: J1.504.911A
• Wikidata: Q76415171
• Mol file: 204254-96-6.mol

Synonyms:204254-96-6;Ethyl (1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate;(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate;ethyl (1S,5R,6S)-5-(1-ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate;EC 429-020-1;Ethyl (3R,4S,5S)-4,5-Epoxy-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate;ethyl (1S,5R,6S)-5-pentan-3-yloxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate;C14H22O4;(1S,5R,6S)-ethyl 5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate;Ethyl (1S,5R,6S)-5-(1-ethylpropoxy)-7-oxabicyclo(4.1.0)hept-3-ene-3-carboxylate;ethyl (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate;7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 5-(1-ethylpropoxy)-, ethyl ester, (1S,5R,6S)-;Ethyl (3R,4S,5S)4,5-Epoxy-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate;EEC- Epoxid;Oseltamivir intermediate;Ethyl(3R,4S,5S)-4,5-Epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate;DFO-5;6T6E34US7J;AMY334;SCHEMBL5182791;DTXSID50942603;BCP11027;AC-417;MFCD08063944;AKOS015895233;CS-T-22794;CS-T-54573;CS-0091283;H10974;EN300-20775814;Z3234882731;(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3ene-3-carboxylate;Ethyl(1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate;(1alpha,6alpha)-5beta-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hepta-3-ene-3-carboxylic acid ethyl ester;(1S,5R,6S)-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester;7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 5-(1-ethylpropoxy)-, ethyl ester, [1S-(1alpha,5beta,6alpha)]-

Chemical Property of Ethyl (1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 56-57 °C
• Refractive Index: 1.492
• Boiling Point: 336.495 °C at 760 mmHg
• Flash Point: 145.075 °C
• PSA: 48.06000
• Density: 1.09 g/cm³
• LogP: 2.22080
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 254.15180918
• Heavy Atom Count: 18
• Complexity: 333

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl(3R,4S,5S)-4,5-Epoxy-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC1C=C(CC2C1O2)C(=O)OCC
• Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@H]2[C@@H]1O2)C(=O)OCC
• Uses: An intermediate of Oseltamivir.

Technology Process of Ethyl (1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate

There total 10 articles about Ethyl (1S,5R,6S)-5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

pentan-3-yl 2,2,2-trichloroacetimidate (949908-55-8) + (1S,5R,6R)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester → (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 10 - 30 ℃; for 16h; Temperature; Solvent;

Reference yield:

ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate (204254-92-2) → (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; at 60 ℃; for 2h;

Reference yield:

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0) → (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; potassium hydrogencarbonate; Yield given. Multistep reaction; 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h;

DOI:10.1021/jo980330q

upstream raw materials:

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate

Downstream raw materials:

ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

ethyl (3R,4R,5S)-4-amino-3-(1-ethylpropoxy)-5-hydroxy-1-cyclohexene-1-carboxylate

ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

(3R,4S,5S)-5-Cyano-3-(1-ethyl-propoxy)-4-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Refernces

• 1、 -. "Method for preparing oseltamivir intermediate". . . Retrieved 2021/06/26.
• 2、 Kongkamnerd, Jarinrat,Cappelletti, Luca,Prandi, Adolfo,Seneci, Pierfausto,Rungrotmongkol, Thanyada,Jongaroonngamsang, Nutthapon,Rojsitthisak, Pornchai,Frecer, Vladimir,Milani, Adelaide,Cattoli, Giovanni,Terregino, Calogero,Capua, Ilaria,Beneduce, Luca,Gallotta, Andrea,Pengo, Paolo,Fassina, Giorgio,Miertus, Stanislav,De-Eknamkul, Wanchai. "Synthesis and in vitro study of novel neuraminidase inhibitors against avian influenza virus". supporting information; experimental part. p. 2152 - 2157. Retrieved 2012/05/05.