5-O-tert-butyl 1-O-ethyl 3-hydroxypentanedioate

Base Information

• Chemical Name: 5-O-tert-butyl 1-O-ethyl 3-hydroxypentanedioate
• CAS No.: 128237-30-9
• Molecular Formula: C11H20 O5
• Molecular Weight: 232.277
• DSSTox Substance ID: DTXSID80390698
• Mol file: 128237-30-9.mol

Synonyms:5-O-tert-butyl 1-O-ethyl 3-hydroxypentanedioate;128237-30-9;tert-Butyl ethyl 3-hydroxypentanedioate;(R)-3-HYDROXYGLUTARATE ETHYL TERT-BUTYL;DTXSID80390698

Chemical Property of 5-O-tert-butyl 1-O-ethyl 3-hydroxypentanedioate

Chemical Property:

• Boiling Point: 317℃
• Flash Point: 112℃
• PSA: 72.83000
• Density: 1.080
• LogP: 1.03230
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 232.13107373
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(CC(=O)OC(C)(C)C)O

Technology Process of 5-O-tert-butyl 1-O-ethyl 3-hydroxypentanedioate

There total 3 articles about 5-O-tert-butyl 1-O-ethyl 3-hydroxypentanedioate 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: 76.5%

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-87-5) + tert-butyl alcohol (75-65-0) → 1-tert-butyl 5-ethyl 3-hydroxypentanedioate (128237-30-9)

Guidance literature:

With thionyl chloride; In dichloromethane; at 0 - 20 ℃;

Reference yield:

tert-butyl ethyl 3-oxopentanedicarboxylate → 1-tert-butyl 5-ethyl 3-hydroxypentanedioate + 1-tert-butyl 5-ethyl 3-hydroxypentanedioate (128237-30-9)

Guidance literature:

With [RuCl(benzene){(2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine)}]Cl; hydrogen; In tetrahydrofuran; at 70 ℃; under 15001.5 Torr; Optical yield = 33.4 %ee; enantioselective reaction; Autoclave;

DOI:10.1002/chem.201202614

Reference yield:

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-87-5) + isobutene (115-11-7,15220-85-6) → 1-tert-butyl 5-ethyl 3-hydroxypentanedioate (128237-30-9)

Guidance literature:

upstream raw materials:

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid

isobutene

tert-butyl alcohol

Downstream raw materials:

tert-butyl (3R)-3-(tert-butyldimethylsilyloxy)-6-dimethoxyphosphinyl-5-oxohexanate

tertiary butyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-(E)-6-heptenoate

rosuvastatin tert-butyl ester