2-Azetidinone, 3-hydroxy-3-methyl-4-phenyl-, (3R,4S)-

Base Information

• Chemical Name: 2-Azetidinone, 3-hydroxy-3-methyl-4-phenyl-, (3R,4S)-
• CAS No.: 182155-36-8
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• DSSTox Substance ID: DTXSID80454209
• Nikkaji Number: J1.161.876F
• Wikidata: Q82275593
• Mol file: 182155-36-8.mol

Synonyms:2-Azetidinone, 3-hydroxy-3-methyl-4-phenyl-, (3R,4S)-;182155-36-8;DTXSID80454209;(3R,4S)-3-Hydroxy-3-methyl-4-phenylazetidine-2-one

Chemical Property of 2-Azetidinone, 3-hydroxy-3-methyl-4-phenyl-, (3R,4S)-

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 223

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(NC1=O)C2=CC=CC=C2)O
• Isomeric SMILES: C[C@]1([C@@H](NC1=O)C2=CC=CC=C2)O

Technology Process of 2-Azetidinone, 3-hydroxy-3-methyl-4-phenyl-, (3R,4S)-

There total 16 articles about 2-Azetidinone, 3-hydroxy-3-methyl-4-phenyl-, (3R,4S)- 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%

(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-3-methyl-4-phenyl-azetidin-2-one (182155-28-8) → (3R,4S)-3-hydroxy-3-methyl-4-phenyl-β-lactam (182155-36-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/0040-4039(96)01420-7

Reference yield: 81.0%

(2S,5R,1'S)-1'-(aminophenylmethyl)-2-tert-butyl-2,5-dimethyl-[1,3]-dioxolan-4-one → (3R,4S)-3-hydroxy-3-methyl-4-phenyl-β-lactam (182155-36-8)

Guidance literature:

With methylmagnesium bromide; In diethyl ether; at 25 ℃; for 1h;

DOI:10.1016/S0957-4166(01)00173-2

Reference yield: 16.0%

(3R,4S)-3-(Dimethyl-phenyl-silanyloxy)-1-(4-methoxy-phenyl)-3-methyl-4-phenyl-azetidin-2-one (209110-55-4) → (3R,4S)-3-hydroxy-3-methyl-4-phenyl-β-lactam (182155-36-8) + (3R,4S)-3-dimethylphenylsilyloxy-3-methyl-4-phenyl-β-lactam (209110-60-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile;

DOI:10.1016/S0040-4039(98)00643-1

upstream raw materials:

(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-3-methyl-4-phenyl-azetidin-2-one

(3R,4S)-3-(Dimethyl-phenyl-silanyloxy)-1-(4-methoxy-phenyl)-3-methyl-4-phenyl-azetidin-2-one

(1'S,2S,5R)-2-(tert-butyl)-5-(1'-amino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one

N-benzylidene-1,1,1-trimethylsilanamine

Downstream raw materials:

(3R,4S)-3-[(triethylsilyl)oxy]-4-(phenyl)-3-methyl-azetidinone

(3R,4S)-3-dimethylphenylsilyloxy-3-methyl-4-phenyl-β-lactam

(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

C₅₉H₈₃NO₁₇Si₂

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