tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate
• CAS No.: 934237-45-3
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309
• Mol file: 934237-45-3.mol

Synonyms:tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate

Chemical Property of tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate

There total 2 articles about tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate 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: 90.0%

(E)-3-phenylpropenal (14371-10-9) + tert-Butyl N-hydroxycarbamate (36016-38-3) → tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate (934237-45-3)

Guidance literature:

With (S)-2-[diphenyl(trimethylsiloxy)methyl)pyrrolidine]; In chloroform; at 20 ℃; for 3h;

DOI:10.1055/s-2007-990935

Reference yield: 85.0%

tert-Butyl N-hydroxycarbamate (36016-38-3) + 3-phenyl-propenal (104-55-2) → tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate (934237-45-3)

Guidance literature:

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In chloroform; at 4 ℃; for 3h; enantioselective reaction;

DOI:10.1002/adsc.201000287

Reference yield: 80.0%

tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate (934237-45-3) → tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate (135865-78-0)

Guidance literature:

With molybdenum hexacarbonyl; In water; acetonitrile; for 16h; Reflux;

DOI:10.1002/adsc.201000287

upstream raw materials:

(E)-3-phenylpropenal

tert-Butyl N-hydroxycarbamate

3-phenyl-propenal

Downstream raw materials:

tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate