(3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine

Base Information

• Chemical Name: (3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine
• CAS No.: 870725-05-6
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.408
• Mol file: 870725-05-6.mol

Synonyms:(3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine

Chemical Property of (3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine

There total 2 articles about (3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine 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:

2-hydroxy-2-methyl-pent-4-en-3-one (22082-43-5) + N-Benzylidenebenzylamine N-oxide (3376-26-9) → 2-benzyl-5-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine + (3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine (870725-05-6) + 2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine

Guidance literature:

With 2,2'-isopropylidenebis<(4S)-4-tert-butyl-4,5-dihydrooxazole>; 4 A molecular sieve; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -20 ℃; for 36h; Title compound not separated from byproducts;

DOI:10.1002/anie.200502308

Reference yield:

3-methoxy-2-methyl-penta-3,4-dien-2-ol (22141-88-4) → (3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine (870725-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / H₂SO₄ / H₂O / 1.5 h / 0 °C

2: Cu(OTf)2; molecular sieves 4 Angstroem; 2,2-bis((4S)-4-tert-butyl-4,5-dihydrooxazol-1-yl)propane / CH₂Cl₂ / 36 h / -20 °C

With 2,2'-isopropylidenebis<(4S)-4-tert-butyl-4,5-dihydrooxazole>; 4 A molecular sieve; sulfuric acid; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; water;

DOI:10.1002/anie.200502308

Reference yield: 96.0%

(3S,4R)-2-benzyl-4-(2-hydroxy-2-methylpropanoyl)-3-phenylisoxazolidine (870725-05-6) + di-tert-butyl dicarbonate (24424-99-5) → (4R,5S)-5-tert-butoxycarbonylamino-2-hydroxy-4-hydroxymethyl-2-methyl-5-phenylpentan-3-one (939959-59-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1002/anie.200502308

upstream raw materials:

2-hydroxy-2-methyl-pent-4-en-3-one

N-Benzylidenebenzylamine N-oxide

3-methoxy-2-methyl-penta-3,4-dien-2-ol

Downstream raw materials:

(4R,5S)-5-tert-butoxycarbonylamino-2-hydroxy-4-hydroxymethyl-2-methyl-5-phenylpentan-3-one