(3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

Base Information

Chemical Name:(3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine
CAS No.:299159-86-7
Molecular Formula:C₁₇H₂₃NO₅
Molecular Weight:321.373
Hs Code.:

Synonyms:(3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

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Chemical Property of (3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

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Technology Process of (3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

There total 5 articles about (3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine 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: 88.0%

: 108-24-7
acetic anhydride

: (3R,4S)-2-Benzyl-3-((R)-2-hydroxy-1-methyl-ethyl)-isoxazolidin-4-ol

: 299159-86-7
(3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 2.5h;
DOI:10.1021/ja000248o

Reference yield:

: (S)-3-(Diphenyl-vinyl-silanyloxy)-2-methyl-propionaldehyde

: 299159-86-7
(3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1: toluene / -78 - 20 °C

2: toluene / 70 °C

3: 77 percent / aq. hydrogen peroxide; potassium hydrogen carbonate; potassium fluoride / methanol; tetrahydrofuran / 2 h / 20 °C

4: 88 percent / Et₃N; DMAP / tetrahydrofuran / 2.5 h / 20 °C

With dmap; potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; toluene; 1: Condensation / 2: Cyclization / 3: oxidative cleavage / 4: Acetylation;
DOI:10.1021/ja000248o

Reference yield:

: 299159-69-6
methyl (2S)-3-diphenylvinylsiloxy-2-methylpropanoate

: 299159-86-7
(3R,4S)-2-benzyl-3-[(1R)-2-acetoxy-1-(methyl)ethyl]-4-acetoxyisoxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: DIBAH / toluene / 0.5 h / -78 °C

2: toluene / -78 - 20 °C

3: toluene / 70 °C

4: 77 percent / aq. hydrogen peroxide; potassium hydrogen carbonate; potassium fluoride / methanol; tetrahydrofuran / 2 h / 20 °C

5: 88 percent / Et₃N; DMAP / tetrahydrofuran / 2.5 h / 20 °C

With dmap; potassium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; toluene; 1: Reduction / 2: Condensation / 3: Cyclization / 4: oxidative cleavage / 5: Acetylation;
DOI:10.1021/ja000248o