Methyl (gammaR)-gamma-hydroxy-3,4-dimethoxybenzenebutanoate

Base Information

• Chemical Name: Methyl (gammaR)-gamma-hydroxy-3,4-dimethoxybenzenebutanoate
• CAS No.: 112022-84-1
• Molecular Formula: C₁₃H₁₈O₅
• Molecular Weight: 254.283
• DSSTox Substance ID: DTXSID601224314
• Mol file: 112022-84-1.mol

Synonyms:DTXSID601224314;Methyl (gammaR)-gamma-hydroxy-3,4-dimethoxybenzenebutanoate;112022-84-1

Chemical Property of Methyl (gammaR)-gamma-hydroxy-3,4-dimethoxybenzenebutanoate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 254.11542367
• Heavy Atom Count: 18
• Complexity: 256

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(CCC(=O)OC)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H](CCC(=O)OC)O)OC

Technology Process of Methyl (gammaR)-gamma-hydroxy-3,4-dimethoxybenzenebutanoate

There total 1 articles about Methyl (gammaR)-gamma-hydroxy-3,4-dimethoxybenzenebutanoate 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:

methyl 4-(3,4-dimethoxyphenyl)-4-oxobutanoate (14563-40-7) → (R)-4-(3,4-Dimethoxy-phenyl)-4-hydroxy-butyric acid methyl ester (112022-84-1)

Guidance literature:

With borane; oxazaborolidine compound ⁽²⁾; at 0 ℃; for 0.5h; Yield given;

DOI:10.1021/ja00259a075

Reference yield: 90.0%

(R)-4-(3,4-Dimethoxy-phenyl)-4-hydroxy-butyric acid methyl ester (112022-84-1) → (R)-5-(3,4-Dimethoxy-phenyl)-dihydro-furan-2-one (112022-85-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1021/ja00259a075

Reference yield:

(R)-4-(3,4-Dimethoxy-phenyl)-4-hydroxy-butyric acid methyl ester (112022-84-1) → (2S,5R)-5-(3,4-Dimethoxy-phenyl)-tetrahydro-furan-2-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaH / tetrahydrofuran / 1 h / 23 °C

2: diisobutylaluminum hydride / toluene / -78 °C

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1021/ja00259a075

upstream raw materials:

methyl 4-(3,4-dimethoxyphenyl)-4-oxobutanoate

Downstream raw materials:

(R)-5-(3,4-Dimethoxy-phenyl)-dihydro-furan-2-one