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

Base Information

• Chemical Name: (1RS,2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol
• CAS No.: 367910-00-7
• Molecular Formula: C₂₃H₃₀O₈
• Molecular Weight: 434.486
• Mol file: 367910-00-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (1RS,2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol 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: 88.0%

(1RS,2S,3R,4R)-3-(tert-butyldiphenylsilyl)oxymethyl-4-methoxymethoxy-4-(3,4-dimethoxyphenyl)-2-methyl-1-(3,4-methylenedioxyphenyl)-1-butanol (367909-99-7) → (1RS,2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol (367910-00-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1271/bbb.65.1559

Reference yield:

(3R,4R)-4-(3,4-dimethoxyphenyl)-3-(pivaloyloxymethyl)-4-butanolide (367909-90-8) → (1RS,2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol (367910-00-7)

Guidance literature:

Multi-step reaction with 11 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

3.1: 88 percent / imidazole / dimethylformamide / 16 h / 20 °C

4.1: diisobutylaluminum hydride / toluene / 0.5 h / -75 °C

5.1: NaBH₄ / ethanol / 1 h / 20 °C

6.1: 0.41 g / pyridine / 1 h / 0 - 5 °C

7.1: 93 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 15 h / 20 °C

8.1: 92 percent / diisobutylaluminum hydride / toluene / 0.5 h / -75 °C

9.1: 90 percent / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

10.1: Mg / tetrahydrofuran / 0.5 h / Heating

10.2: 89 percent / tetrahydrofuran / 1 h / 0 °C

11.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; magnesium; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1271/bbb.65.1559

Reference yield:

(2S,3R,4R)-4-(3,4-dimethoxyphenyl)-2-methyl-3-pivaloyloxymethyl-4-butanolide (367909-91-9) → (1RS,2S,3R)-3-[(1R)-1-methoxymethoxy-1-(3,4-dimethoxyphenyl)methyl]-2-methyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol (367910-00-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 55 percent / aq. NaOH / ethanol / 16 h / 20 °C

2.1: 88 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: diisobutylaluminum hydride / toluene / 0.5 h / -75 °C

4.1: NaBH₄ / ethanol / 1 h / 20 °C

5.1: 0.41 g / pyridine / 1 h / 0 - 5 °C

6.1: 93 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 15 h / 20 °C

7.1: 92 percent / diisobutylaluminum hydride / toluene / 0.5 h / -75 °C

8.1: 90 percent / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

9.1: Mg / tetrahydrofuran / 0.5 h / Heating

9.2: 89 percent / tetrahydrofuran / 1 h / 0 °C

10.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; magnesium; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1271/bbb.65.1559

upstream raw materials:

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

1,2-(methylenedioxy)-4-bromobenzene

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

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

Downstream raw materials:

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