2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester

Base Information

• Chemical Name: 2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester
• CAS No.: 461435-05-2
• Molecular Formula: C₉H₉IO₅
• Molecular Weight: 324.072
• Mol file: 461435-05-2.mol

Synonyms:2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester

Chemical Property of 2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester

There total 1 articles about 2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl 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: 80.0%

2,4-Dihydroxy-3-hydroxymethyl-benzoic acid methyl ester (182744-65-6) → 2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester (461435-05-2)

Guidance literature:

With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate; In methanol; for 2.75h;

DOI:10.1021/ol026382q

Reference yield:

2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester (461435-05-2) → epi-C2'-Luminacin D

Guidance literature:

Multi-step reaction with 12 steps

1.1: K₂CO₃ / acetone / 24 h / Heating

2.1: 4.30 g / imidazole / dimethylformamide / 24 h

3.1: 85 percent / (o-tol)3P / trans-ClBnPd(PPh₃)2 / dimethylformamide / 24 h / 100 °C

4.1: DIBAL / CH₂Cl₂ / 3 h / -78 °C

5.1: 4.65 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: t-butyllithium / diethyl ether; pentane / 0.58 h / -78 °C

6.2: diethyl ether; pentane / -78 °C

7.1: 1.23 g / Dess-Martin periodinane / CH₂Cl₂ / 0.08 h

8.1: 79 percent / TBAF / tetrahydrofuran / 10 h / 0 °C

9.1: 86 percent / VO(acac)2; TBHP / toluene; benzene / 2 h

10.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.08 h

11.1: 44 percent / acetic acid / tetrahydrofuran; H₂O / 3 h / Heating

12.1: H₂ / Pd/C / ethyl acetate / 5 h / 760.05 Torr

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II); In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; pentane; benzene; 3.1: Stille cross-coupling / 7.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation;

DOI:10.1021/ol026382q

Reference yield:

2,4-dihydroxy-3-hydroxymethyl-5-iodo-benzoic acid methyl ester (461435-05-2) → (+/-)-luminacin D

Guidance literature:

Multi-step reaction with 12 steps

1.1: K₂CO₃ / acetone / 24 h / Heating

2.1: 4.30 g / imidazole / dimethylformamide / 24 h

3.1: 85 percent / (o-tol)3P / trans-ClBnPd(PPh₃)2 / dimethylformamide / 24 h / 100 °C

4.1: DIBAL / CH₂Cl₂ / 3 h / -78 °C

5.1: 4.65 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: t-butyllithium / diethyl ether; pentane / 0.58 h / -78 °C

6.2: diethyl ether; pentane / -78 °C

7.1: 1.23 g / Dess-Martin periodinane / CH₂Cl₂ / 0.08 h

8.1: 79 percent / TBAF / tetrahydrofuran / 10 h / 0 °C

9.1: 86 percent / VO(acac)2; TBHP / toluene; benzene / 2 h

10.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.08 h

11.1: 44 percent / acetic acid / tetrahydrofuran; H₂O / 3 h / Heating

12.1: H₂ / Pd/C / ethyl acetate / 5 h / 760.05 Torr

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II); In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; pentane; benzene; 3.1: Stille cross-coupling / 7.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation;

DOI:10.1021/ol026382q

upstream raw materials:

2,4-Dihydroxy-3-hydroxymethyl-benzoic acid methyl ester

Downstream raw materials:

2,4-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-(2-methyl-propenyl)-benzaldehyde

2,4-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-iodo-benzoic acid methyl ester

2,4-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-(2-methyl-propenyl)-benzoic acid methyl ester