(1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester
• CAS No.: 103477-65-2
• Molecular Formula: C₂₅H₃₀O₉
• Molecular Weight: 474.508
• Mol file: 103477-65-2.mol

Synonyms:(1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester

Chemical Property of (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester

There total 9 articles about (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl 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: 82.0%

cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide (103477-62-9) + dimethylfumarate (624-49-7) → (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester (103477-65-2)

Guidance literature:

With zinc(II) oxide; In benzene; for 15h; Heating;

DOI:10.1021/jo00368a018

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester (103477-65-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / Br₂, CH₃COOH / 5 h / Ambient temperature

2: 98 percent / p-toluenosulfonic acid / benzene / 2 h / Heating

3: 1.) tetramethylene diamine, n-butyllithium, (n-Bu)3P*CuI / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 0.5 h

4: 95 percent / 10percent aq. HCl / diethyl ether / 2 h / Ambient temperature

5: 67 percent / SO₂ / thiophene / 8 h / Irradiation

6: p-toluenosulfonic acid / CH₂Cl₂ / 1 h / Heating

7: 82 percent / ZnO / benzene / 15 h / Heating

With hydrogenchloride; n-butyllithium; CuI*P(n-Bu)3; N,N,N,N,-tetramethylethylenediamine; sulfur dioxide; bromine; toluene-4-sulfonic acid; acetic acid; zinc(II) oxide; In thiophene; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00368a018

Reference yield:

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) → (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester (103477-65-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) tetramethylene diamine, n-butyllithium, (n-Bu)3P*CuI / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 0.5 h

2: 95 percent / 10percent aq. HCl / diethyl ether / 2 h / Ambient temperature

3: 67 percent / SO₂ / thiophene / 8 h / Irradiation

4: p-toluenosulfonic acid / CH₂Cl₂ / 1 h / Heating

5: 82 percent / ZnO / benzene / 15 h / Heating

With hydrogenchloride; n-butyllithium; CuI*P(n-Bu)3; N,N,N,N,-tetramethylethylenediamine; sulfur dioxide; toluene-4-sulfonic acid; zinc(II) oxide; In thiophene; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00368a018

upstream raw materials:

cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide

dimethylfumarate

4-bromomethyl-1,2-dimethoxybenzene

2-bromo-4,5-dimethoxybenzaldehyde

Downstream raw materials:

dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate

dimethyl trans-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,2-dihydronaphthalene-2,3-dicarboxylate

r-1-(3,4-dimethoxyphenyl)-t-2,c-3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene