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

Base Information

• Chemical Name: methyl 2-{(2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate
• CAS No.: 930285-54-4
• Molecular Formula: C₃₆H₄₉NO₈Si
• Molecular Weight: 651.872
• Mol file: 930285-54-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about methyl 2-{(2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate 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-((2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-hydroxyhex-5-ynyl)-4,6-dimethoxybenzoate (930285-53-3) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → methyl 2-{(2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate (930285-54-4)

Guidance literature:

With Proton Sponge; In dichloromethane; at -60 - 20 ℃;

DOI:10.1021/ol0629317

Reference yield:

2-allyl-4,6-dimethoxybenzoic acid (930285-77-1) → methyl 2-{(2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate (930285-54-4)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ol0629317

Reference yield:

2,4 dimethoxybenzoic acid (91-52-1) → methyl 2-{(2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-[(triisopropylsilyl)oxy]hex-5-ynyl}-4,6-dimethoxybenzoate (930285-54-4)

Guidance literature:

Multi-step reaction with 6 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

With 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; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; 5.3: Evans aldol reaction;

DOI:10.1021/ol0629317

upstream raw materials:

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

triisopropylsilyl trifluoromethanesulfonate

(4S)-4-benzyl-3-pent-4-ynoyl-oxazolidin-2-one

2-allyl-4,6-dimethoxybenzoic acid

Downstream raw materials:

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

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

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

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