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

Base Information

• Chemical Name: (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide
• CAS No.: 367909-92-0
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 367909-92-0.mol

Synonyms:(2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide

Chemical Property of (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide

There total 2 articles about (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-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: 55.0%

(2S,3R,4R)-4-(3,4-dimethoxyphenyl)-2-methyl-3-pivaloyloxymethyl-4-butanolide (367909-91-9) → (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide (367909-92-0) + (2S,3R)-3-[(1R)-1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-4-butanolide (367909-93-1)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1271/bbb.65.1559

Reference yield:

(3R,4R)-4-(3,4-dimethoxyphenyl)-3-(pivaloyloxymethyl)-4-butanolide (367909-90-8) → (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide (367909-92-0)

Guidance literature:

Multi-step reaction with 2 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: 55 percent / aq. NaOH / ethanol / 16 h / 20 °C

With sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;

DOI:10.1271/bbb.65.1559

Reference yield: 88.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2S,3R,4R)-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide (367909-92-0) → (2S,3R,4R)-3-(tert-butyldiphenylsilyl)oxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide (367909-94-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1271/bbb.65.1559

upstream raw materials:

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

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

Downstream raw materials:

(2S,3R,4R)-3-(tert-butyldiphenylsilyl)oxymethyl-4-(3,4-dimethoxyphenyl)-2-methyl-4-butanolide

(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

(1RS,2S,3R,4R)-3-(tert-butyldiphenylsilyl)oxymethyl-4-methoxymethoxy-4-(3,4-dimethoxyphenyl)-2-methyl-1-(3,4-methylenedioxyphenyl)-1-butanol