(4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Name:(4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:190730-58-6
Molecular Formula:C₂₁H₃₀BrNO₄Si
Molecular Weight:468.463
Hs Code.:

Synonyms:(4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 3 articles about (4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 190730-57-5
(+)-4(R)-methyl-5(S)-phenyl-3-(4-bromo-3(R)-hydroxy-4-pentenoyl)-2-oxazolidinone

: 190730-58-6
(4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 4h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00412-2

Reference yield:

: 135793-05-4,113122-37-5
(4R,5S)-3-(2-chloroacetyl)-4-methyl-5-phenyloxazolidin-2-one

: 190730-58-6
(4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) Bu₂BOTf, i-Pr₂NEt, 3.) H₂O₂

2: 80 percent / Zn, NH₄Cl / methanol / 6 h / Ambient temperature

3: 97 percent / 2,6=lutidine / CH₂Cl₂ / 4 h / Ambient temperature

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; ammonium chloride; N-ethyl-N,N-diisopropylamine; zinc; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(97)00412-2

Reference yield:

: 190730-56-4
(+)-4(R)-methyl-5(S)-phenyl-3-(4-bromo-2(R)-chloro-3(R)-hydroxy-4-pentenoyl)-2-oxazolidinone

: 190730-58-6
(4R,5S)-3-[(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / Zn, NH₄Cl / methanol / 6 h / Ambient temperature

2: 97 percent / 2,6=lutidine / CH₂Cl₂ / 4 h / Ambient temperature

With 2,6-dimethylpyridine; ammonium chloride; zinc; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(97)00412-2