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

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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
Hs Code.:

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

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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

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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%

: 930285-53-3
methyl 2-((2R,3S)-3-{[(4S)-4-benzyl-2-oxo-oxazolidin-3-yl]carbonyl}-2-hydroxyhex-5-ynyl)-4,6-dimethoxybenzoate

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

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

Guidance literature:: With Proton Sponge; In dichloromethane; at -60 - 20 ℃;
DOI:10.1021/ol0629317

Reference yield:

: 930285-77-1
2-allyl-4,6-dimethoxybenzoic acid

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

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:

: 91-52-1
2,4 dimethoxybenzoic acid

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

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