ethyl (3aR,7R,7aR)-2,2-diethyl-7-methylsulfonyloxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate

Base Information

• Chemical Name: ethyl (3aR,7R,7aR)-2,2-diethyl-7-methylsulfonyloxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate
• CAS No.: 204254-90-0
• Molecular Formula: C15H24O7S
• Molecular Weight: 348.417
• European Community (EC) Number: 606-549-8
• DSSTox Substance ID: DTXSID601110181
• Wikidata: Q76414768
• Mol file: 204254-90-0.mol

Synonyms:204254-90-0;ethyl (3aR,7R,7aR)-2,2-diethyl-7-methylsulfonyloxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate;SCHEMBL1255202;ACWOABVIOKTVCQ-JHJVBQTASA-N;DTXSID601110181;CS-0164994;Oseltamivir Impurity 58 (Oseltamivir Impurity pound(c);Ethyl (3aR,7R,7aR)-2,2-diethyl-3a,6,7,7a-tetrahydro-7-[(methylsulfonyl)oxy]-1,3-benzodioxole-5-carboxylate;ethyl (3aR,7R,7aR)-2,2-diethyl-7-(methanesulfonyloxy)-3a,6,7,7a-tetrahydro-2H-1,3-benzodioxole-5-carboxylate

Chemical Property of ethyl (3aR,7R,7aR)-2,2-diethyl-7-methylsulfonyloxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 474.211°C at 760 mmHg
• Flash Point: 240.594°C
• PSA: 96.51000
• Density: 1.267g/cm³
• LogP: 2.60550
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 348.12427427
• Heavy Atom Count: 23
• Complexity: 571

Purity/Quality:

98% ^*data from raw suppliers

(3aR,7R,7aR)-2,2-Diethyl-3a,6,7,7a-tetrahydro-7-[(methylsulfonyl)oxy]-1,3-benzodioxole-5-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1(OC2C=C(CC(C2O1)OS(=O)(=O)C)C(=O)OCC)CC
• Isomeric SMILES: CCC1(O[C@@H]2C=C(C[C@H]([C@@H]2O1)OS(=O)(=O)C)C(=O)OCC)CC
• Uses: (3aR,7R,7aR)-2,2-Diethyl-3a,6,7,7a-tetrahydro-7-[(methylsulfonyl)oxy]-1,3-benzodioxole-5-carboxylic Acid Ethyl Ester is an analog of (1R,5S,6S)-rel-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Methyl Ester (E925665) which is an intermediate in the synthesis of neuraminidase inhibitors.

Technology Process of ethyl (3aR,7R,7aR)-2,2-diethyl-7-methylsulfonyloxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate

There total 9 articles about ethyl (3aR,7R,7aR)-2,2-diethyl-7-methylsulfonyloxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-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: 98.0%

pentan-3-one (96-22-0) + ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-84-2) → ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0)

Guidance literature:

With trifluoroacetic acid; at 40 ℃; for 1h; under 75007.5 - 112511 Torr; Inert atmosphere; Industrial scale; Large scale;

DOI:10.1021/op9900176

Reference yield: 95.0%

(3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate (943515-58-0) + methanesulfonyl chloride (124-63-0) → ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2012.01.026

Reference yield:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester (101769-63-5) → ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (204254-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / water; toluene / 0.25 h / 100 °C / Molecular sieve; Microwave irradiation

2: triethylamine / dichloromethane / 0 - 20 °C

With toluene-4-sulfonic acid; triethylamine; In dichloromethane; water; toluene;

DOI:10.1016/j.bmc.2012.01.026

upstream raw materials:

pentan-3-one

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

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

methanesulfonyl chloride

Downstream raw materials:

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

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

ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

oseltamivir

Refernces

• 1、 -. "METHOD FOR PREVENTING OR TREATING ARRHYTHMIA, METHOD FOR PREVENTING OR TREATING ATRIAL FIBRILLATION, MODEL OF SUSTAINED ATRIAL FIBRILLATION, METHOD FOR PRODUCING THE MODEL, AND METHOD FOR SCREENING FOR ATRIAL FIBRILLATION INHIBITOR". Paragraph 0095. . Retrieved 2014/03/24.
• 2、 -. "EPOXIDE INTERMEDIATE IN THE TAMIFLU SYNTHESIS". Page/Page column 18; 22. . Retrieved 2008/06/13.