(2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide

Base Information

• Chemical Name: (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide
• CAS No.: 367910-01-8
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• Mol file: 367910-01-8.mol

Synonyms:(2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide

Chemical Property of (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide

There total 3 articles about (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide 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: 87.0%

chloromethyl methyl ether (107-30-2) + (2S,3R)-3-[(1R)-1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide (367909-93-1) → (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide (367910-01-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1271/bbb.65.1559

Reference yield:

(3R,4R)-4-(3,4-dimethoxyphenyl)-3-(pivaloyloxymethyl)-4-butanolide (367909-90-8) → (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide (367910-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / -75 °C

1.2: 88 percent / tetrahydrofuran / 0.5 h / -75 °C

2.1: 37 percent / aq. NaOH / ethanol / 16 h / 20 °C

3.1: 87 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1271/bbb.65.1559

Reference yield:

(2S,3R,4R)-4-(3,4-dimethoxyphenyl)-2-methyl-3-pivaloyloxymethyl-4-butanolide (367909-91-9) → (2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide (367910-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / aq. NaOH / ethanol / 16 h / 20 °C

2: 87 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;

DOI:10.1271/bbb.65.1559

upstream raw materials:

chloromethyl methyl ether

(2S,3R)-3-[(1R)-1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide

(3R,4R)-4-(3,4-dimethoxyphenyl)-3-(pivaloyloxymethyl)-4-butanolide

(2S,3R,4R)-4-(3,4-dimethoxyphenyl)-2-methyl-3-pivaloyloxymethyl-4-butanolide

Downstream raw materials:

(2S,3S,4R)-4-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-3-methyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

(1RS,2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol