(3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS No.: 154306-81-7
• Molecular Formula: C17H17NO2
• Molecular Weight: 267.327
• European Community (EC) Number: 604-945-5
• DSSTox Substance ID: DTXSID90514186
• Wikidata: Q82374364
• Mol file: 154306-81-7.mol

Synonyms:154306-81-7;(3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one;SCHEMBL8829721;DTXSID90514186

Chemical Property of (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one

Chemical Property:

• Vapor Pressure: 4.55E-10mmHg at 25°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 267.125928785
• Heavy Atom Count: 20
• Complexity: 345

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)N2C(C(C2=O)O)C3=CC=CC=C3
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)N2[C@H]([C@H](C2=O)O)C3=CC=CC=C3

Technology Process of (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one

There total 6 articles about (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-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: 67.0%

Acetic acid (3S,4R)-2-oxo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-3-yl ester → (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one (154306-81-7) + (3S,4R)-3-Hydroxy-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)61724-0

Reference yield:

methyl (2R,3S)-2-methoxy-3-phenyl-3-<(S)-methylbenzylamino>propanoate (212764-79-9) → (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one (154306-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / BBr₃ / -78 °C

2: BBr₃ / 0 °C

With boron tribromide;

DOI:10.1016/S0960-894X(98)00271-6

Reference yield:

(3R,4S)-3-methoxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one (212764-84-6) → (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one (154306-81-7)

Guidance literature:

With boron tribromide; at 0 ℃;

DOI:10.1016/S0960-894X(98)00271-6

upstream raw materials:

(3R,4S)-3-methoxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one

N-benzylidene-(S)-α-methylbenzylamine

methyl (2R,3S)-2-methoxy-3-phenyl-3-<(S)-methylbenzylamino>propanoate

Downstream raw materials:

methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate

(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate