2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid

Base Information

• Chemical Name: 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid
• CAS No.: 930285-58-8
• Molecular Formula: C₂₅H₄₀O₅Si
• Molecular Weight: 448.675
• Mol file: 930285-58-8.mol

Synonyms:2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid

Chemical Property of 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid

There total 10 articles about 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid 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: 95.0%

methyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoate (930285-57-7) → 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid (930285-58-8)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 20h; Heating;

DOI:10.1021/ol0629317

Reference yield:

2-allyl-4,6-dimethoxybenzoic acid (930285-77-1) → 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid (930285-58-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 14.45 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 20 °C

2.1: 4-methylmorpholine N-oxide; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

3.1: 6.3 g / NaIO₄ / methanol; H₂O / 2 h / 20 °C

4.1: nBu₂BOTf / toluene; CH₂Cl₂ / 0.08 h / -10 °C

4.2: iPr₂NEt / toluene; CH₂Cl₂ / 2 h / 0 °C

4.3: 85 percent / toluene; CH₂Cl₂ / -78 - 0 °C

5.1: 95 percent / proton sponge / CH₂Cl₂ / -60 - 20 °C

6.1: 94 percent / NaBH₄ / tetrahydrofuran; H₂O / 73 h / 0 - 20 °C

7.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

8.1: 97 percent / sodium iodide; zinc / 1,2-dimethoxy-ethane / 4 h / Heating

9.1: 95 percent / KOH / ethanol; H₂O / 20 h / Heating

With dmap; potassium hydroxide; sodium tetrahydroborate; sodium periodate; Proton Sponge; di-n-butylboryl trifluoromethanesulfonate; water; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc; osmium(VIII) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 4.3: Evans aldol reaction;

DOI:10.1021/ol0629317

Reference yield:

2,4 dimethoxybenzoic acid (91-52-1) → 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoic acid (930285-58-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sBuLi; TMEDA / tetrahydrofuran; cyclohexane / 1.5 h / -90 - -78 °C

1.2: tetrahydrofuran; cyclohexane / 1.5 h / cooling

2.1: 14.45 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 20 °C

3.1: 4-methylmorpholine N-oxide; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

4.1: 6.3 g / NaIO₄ / methanol; H₂O / 2 h / 20 °C

5.1: nBu₂BOTf / toluene; CH₂Cl₂ / 0.08 h / -10 °C

5.2: iPr₂NEt / toluene; CH₂Cl₂ / 2 h / 0 °C

5.3: 85 percent / toluene; CH₂Cl₂ / -78 - 0 °C

6.1: 95 percent / proton sponge / CH₂Cl₂ / -60 - 20 °C

7.1: 94 percent / NaBH₄ / tetrahydrofuran; H₂O / 73 h / 0 - 20 °C

8.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

9.1: 97 percent / sodium iodide; zinc / 1,2-dimethoxy-ethane / 4 h / Heating

10.1: 95 percent / KOH / ethanol; H₂O / 20 h / Heating

With dmap; potassium hydroxide; sodium tetrahydroborate; sodium periodate; Proton Sponge; N,N,N,N,-tetramethylethylenediamine; di-n-butylboryl trifluoromethanesulfonate; water; sec.-butyllithium; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc; osmium(VIII) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; 5.3: Evans aldol reaction;

DOI:10.1021/ol0629317

upstream raw materials:

methyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hex-5-ynyl}benzoate

methyl 2-((2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-hydroxyhex-5-ynyl)-4,6-dimethoxybenzoate

methyl 2-{(2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate

methyl 2-{(2R,3R)-3-(hydroxymethyl)-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate

Downstream raw materials:

2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoic acid

C₂₉H₄₄N₂O₄Si

C₄₇H₇₂O₉Si

(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate