(3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester

Base Information

• Chemical Name: (3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester
• CAS No.: 204254-92-2
• Molecular Formula: C15H26O7S
• Molecular Weight: 350.433
• UNII: 4F6KD39DMX
• Mol file: 204254-92-2.mol

Synonyms:204254-92-2;Ethyl (3R,4R,5R)-4-hydroxy-5-methylsulfonyloxy-3-pentan-3-yloxycyclohexene-1-carboxylate;(3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethy;(3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester;Oseltamivir Impurity 59;4F6KD39DMX;SCHEMBL1255103;(3R,4R,5R)-Ethyl 4-hydroxy-5-((methylsulfonyl)oxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate;1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3-(1-ETHYLPROPOXY)-4-HYDROXY-5-[(METHYLSULFONYL)OXY]-, ETHYL ESTER, (3R,4R,5R)-;1-Cyclohexene-1-carboxylic acid, 3-(1-ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-, ethyl ester, [3R-(3alpha,4alpha,5beta)]-;Ethyl (3R,4R,5R)-3-(1-ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylate;ETHYL (3R,4R,5R)-4-HYDROXY-5-(METHANESULFONYLOXY)-3-(PENTAN-3-YLOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE

Chemical Property of (3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester

Chemical Property:

• Melting Point: 66-68°C
• PSA: 107.51000
• LogP: 2.23990
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 350.13992434
• Heavy Atom Count: 23
• Complexity: 516

Purity/Quality:

98% ^*data from raw suppliers

(3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC1C=C(CC(C1O)OS(=O)(=O)C)C(=O)OCC
• Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@H]([C@@H]1O)OS(=O)(=O)C)C(=O)OCC
• Uses: (3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(Methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester is used in the synthesis of novel neuraminidase inhibitors as avian influenza anti-viral agents. This compound is used in the synthesis of novel neuraminidase inhibitors as avian influenza anti-viral agents.

Technology Process of (3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester

There total 21 articles about (3R,4R,5R)-3-(1-Ethylpropoxy)-4-hydroxy-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylic Acid Ethyl Ester 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: 99.7%

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0) → ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate (204254-92-2)

Guidance literature:

With triethylsilane; titanium tetrachloride; In dichloromethane; at -15 ℃; for 0.333333h; Temperature;

Reference yield:

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0) → (3R,4R,5R)-3,4-Dihydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester + ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate (204254-92-2)

Guidance literature:

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate; With triethylsilane; titanium tetrachloride; In dichloromethane; at -35 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In dichloromethane; at 0 ℃; pH=10; Inert atmosphere;

DOI:10.1016/j.bmc.2012.01.026

Reference yield:

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0) → (3R,4R,5R)-4-(1-Ethyl-propoxy)-3-hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester + ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate (204254-92-2)

Guidance literature:

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate; With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; In dichloromethane; at -30 - -20 ℃; for 1h;

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 12h;

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

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

(3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate

Downstream raw materials:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Refernces

• 1、 -. "Continuous synthesis method of oseltamivir phosphate intermediate". Paragraph 0029-0046. . Retrieved 2019/09/10.
• 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". . p. 2152 - 2157. Retrieved 2012/05/05.