(R)-3-Acetoxybutyric acid tert-butyl ester

Base Information

• Chemical Name: (R)-3-Acetoxybutyric acid tert-butyl ester
• CAS No.: 120444-06-6
• Molecular Formula: C10H18O4
• DSSTox Substance ID: DTXSID601253864
• Nikkaji Number: J1.551.484A
• Mol file: 120444-06-6.mol

Synonyms:(R)-3-Acetoxybutyric acid tert-butyl ester;120444-06-6;DTXSID601253864;1,1-Dimethylethyl (3R)-3-(acetyloxy)butanoate

Chemical Property of (R)-3-Acetoxybutyric acid tert-butyl ester

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 202.12050905
• Heavy Atom Count: 14
• Complexity: 215

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)OC(C)(C)C)OC(=O)C
• Isomeric SMILES: C[C@H](CC(=O)OC(C)(C)C)OC(=O)C

Technology Process of (R)-3-Acetoxybutyric acid tert-butyl ester

There total 1 articles about (R)-3-Acetoxybutyric acid tert-butyl 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: 94.0%

Isopropenyl acetate (108-22-5) + tert-butyl 3-hydroxybutyrate (90435-23-7) → tert-butyl (S)-3-hydroxybutyrate (82578-45-8) + tert-butyl (R)-3-hydroxybutanoate (110171-06-7) + (R)-3-acetoxy-butyric acid tert-butyl ester (120444-06-6)

Guidance literature:

With Pseudomonas cepacia lipase immobilized on ceramic; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η⁵-C4CNH(i-Pr))]Ru(CO)2Cl; In toluene; at 25 ℃; for 120h;

DOI:10.1021/jo0355799

Reference yield:

(R)-3-acetoxy-butyric acid tert-butyl ester (120444-06-6) → (R,R,R,R,R,R,R,R)-α-benzyl-ω-(tert-butoxy)octakis (152996-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1: sat. Na₂CO₃ / methanol / Ambient temperature

2: pyridine / CH₂Cl₂ / -78 °C / to RT

3: 93 percent / H₂ / Pd/C / ethanol; acetic acid / 5 h / Ambient temperature

4: pyridine / CH₂Cl₂ / -78 °C / to RT

5: 99 percent / H₂ / Pd/C / ethyl acetate; acetic acid / Ambient temperature

6: pyridine / CH₂Cl₂ / -78 °C / to RT

With pyridine; hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid; ethyl acetate;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2430::AID-HLCA2430>3.0.CO;2-W

Reference yield:

(R)-3-acetoxy-butyric acid tert-butyl ester (120444-06-6) → (3R)-3-<<(3'R)-3'-<<(3''S)-3''-<<(3'''S)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester (220095-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sat. Na₂CO₃ / methanol / Ambient temperature

2: pyridine / CH₂Cl₂ / -78 °C / to RT

3: 93 percent / H₂ / Pd/C / ethanol; acetic acid / 5 h / Ambient temperature

4: pyridine / CH₂Cl₂ / -78 °C / to RT

With pyridine; hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2430::AID-HLCA2430>3.0.CO;2-W

upstream raw materials:

Isopropenyl acetate

tert-butyl 3-hydroxybutyrate

Downstream raw materials:

tert-butyl (R)-3-hydroxybutanoate

(3R)-3-<<(3'R)-3'-(benzyloxy)butanoyl>oxy>butanoic acid tert-butyl ester

(3R)-3-<<(3'R)-3'-<<(3R)-3-<<(3'R)-3'-(benzyloxy)butyryl>oxy>butyryl>oxy>butyryl>oxy>butyric acid-(tert-butyl)ester

(R,R,R,R,R,R,R,R)-α-benzyl-ω-(tert-butoxy)octakis

Refernces