Diacetic acid 2-[2-(methylsulfonyloxy)ethyl]-1,3-propanediyl ester

Base Information

• Chemical Name: Diacetic acid 2-[2-(methylsulfonyloxy)ethyl]-1,3-propanediyl ester
• CAS No.: 128139-38-8
• Molecular Formula: C10H18O7S
• Molecular Weight: 282.315
• European Community (EC) Number: 603-259-3
• DSSTox Substance ID: DTXSID401160504
• Nikkaji Number: J2.321.213G
• Mol file: 128139-38-8.mol

Synonyms:SCHEMBL6577422;DTXSID401160504;Diacetic acid 2-[2-(methylsulfonyloxy)ethyl]-1,3-propanediyl ester;1,4-Butanediol, 2-[(acetyloxy)methyl]-, 1-acetate 4-methanesulfonate;128139-38-8

Chemical Property of Diacetic acid 2-[2-(methylsulfonyloxy)ethyl]-1,3-propanediyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.46
• Boiling Point: 416.679°C at 760 mmHg
• Flash Point: 205.8°C
• PSA: 104.35000
• Density: 1.236g/cm³
• LogP: 1.17590
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 282.07732408
• Heavy Atom Count: 18
• Complexity: 350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(CCOS(=O)(=O)C)COC(=O)C

Technology Process of Diacetic acid 2-[2-(methylsulfonyloxy)ethyl]-1,3-propanediyl ester

There total 6 articles about Diacetic acid 2-[2-(methylsulfonyloxy)ethyl]-1,3-propanediyl 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:

1,3-diacetoxy-2-(2-hydroxyethyl)propane (126589-88-6) + methanesulfonyl chloride (124-63-0) → Acetic acid 2-acetoxymethyl-4-methanesulfonyloxy-butyl ester (128139-38-8)

Guidance literature:

With triethylamine; In dichloromethane; at -5 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4020(01)87878-9

Reference yield:

2-(2-(benzyloxy)ethyl)propane-1,3-diol (77661-80-4) → Acetic acid 2-acetoxymethyl-4-methanesulfonyloxy-butyl ester (128139-38-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 1 h / 0 °C

2: H₂ / 10percent Pd/C / ethanol / 18 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / -5 °C

With pyridine; dmap; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)87878-9

Reference yield:

2-acetoxymethyl-4-benzyloxybutyl acetate (131266-10-9) → Acetic acid 2-acetoxymethyl-4-methanesulfonyloxy-butyl ester (128139-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethanol / 18 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 1 h / -5 °C

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)87878-9

upstream raw materials:

1,3-diacetoxy-2-(2-hydroxyethyl)propane

methanesulfonyl chloride

1-acetoxy-2-acetoxymethyl-4-(1-ethoxyethoxy)butane

diethyl <2-(1-ethoxyethoxy)ethyl>malonate

Downstream raw materials:

7-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine

9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-iodopurine

9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-bromopurine

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine

Refernces

• 1、 Brand, Briony,Reese, Colin B.,Song, Quanlai,Visintin, Cristina. "Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9h-purine (famciclovir)". . p. 5239 - 5252. Retrieved 2007/10/03.