(4-Nitrophenyl)methyl (alphaR,2R,3S)-2-(2-benzothiazolyldithio)-3-bromo-alpha-(1-methylethenyl)-4-oxo-1-azetidineacetate

Base Information

• Chemical Name: (4-Nitrophenyl)methyl (alphaR,2R,3S)-2-(2-benzothiazolyldithio)-3-bromo-alpha-(1-methylethenyl)-4-oxo-1-azetidineacetate
• CAS No.: 95122-89-7
• Molecular Formula: C₂₂H₁₈BrN₃O₅S₃
• Molecular Weight: 580.504
• European Community (EC) Number: 619-109-5
• DSSTox Substance ID: DTXSID601107829
• Mol file: 95122-89-7.mol

Synonyms:SCHEMBL2924737;UPVOZBVZWJUNLP-NLWGTHIKSA-N;DTXSID601107829;(4-Nitrophenyl)methyl (alphaR,2R,3S)-2-(2-benzothiazolyldithio)-3-bromo-alpha-(1-methylethenyl)-4-oxo-1-azetidineacetate;95122-89-7;p-nitrobenzyl (2r)-2-[(3s,4r)-4-(benzothiazol-2-yldithio)-3-bromo-2-oxoazetidin-1-yl]-3-methylbut-3-enoate

Chemical Property of (4-Nitrophenyl)methyl (alphaR,2R,3S)-2-(2-benzothiazolyldithio)-3-bromo-alpha-(1-methylethenyl)-4-oxo-1-azetidineacetate

Chemical Property:

• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 578.95920
• Heavy Atom Count: 34
• Complexity: 807

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=C)C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])N2C(C(C2=O)Br)SSC3=NC4=CC=CC=C4S3
• Isomeric SMILES: CC(=C)[C@H](C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])N2[C@@H]([C@H](C2=O)Br)SSC3=NC4=CC=CC=C4S3

Technology Process of (4-Nitrophenyl)methyl (alphaR,2R,3S)-2-(2-benzothiazolyldithio)-3-bromo-alpha-(1-methylethenyl)-4-oxo-1-azetidineacetate

There total 7 articles about (4-Nitrophenyl)methyl (alphaR,2R,3S)-2-(2-benzothiazolyldithio)-3-bromo-alpha-(1-methylethenyl)-4-oxo-1-azetidineacetate 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: 99.0%

2-Mercaptobenzothiazole (149-30-4,118090-09-8) + p-nitrobenzoyl 6α-bromopenicillanate 1-oxide (79634-01-8) → p-nitrobenzyl 2-<2-oxo-3α-bromo-4-(benzothiazol-2-yldithio)azetidin-1-yl>-2-isopropenylacetate (95122-89-7)

Guidance literature:

In 1,4-dioxane; for 3.5h; Heating;

DOI:10.1021/jm00382a025

Reference yield: 98.0%

6-bromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide p-nitrobenzyl ester (847871-87-8) + 2-Mercaptobenzothiazole (149-30-4,118090-09-8) → p-nitrobenzyl 2-<2-oxo-3α-bromo-4-(benzothiazol-2-yldithio)azetidin-1-yl>-2-isopropenylacetate (95122-89-7)

Guidance literature:

In toluene;

Reference yield: 88.9%

2-Mercaptobenzothiazole (149-30-4,118090-09-8) + p-nitrobenzoyl 6α-bromopenicillanate 1-oxide (79634-01-8) → 2-(2-benzothiazolyldithio)-3-bromo-α-(1-methylethylidene)-4-oxo-1-azetidineacetic acid β-nitrobenzyl ester (95122-89-7,126577-33-1)

Guidance literature:

In water; toluene; at 86 - 90 ℃; for 3 - 4h; under 337.534 - 375.038 Torr;

upstream raw materials:

2-Mercaptobenzothiazole

p-nitrobenzoyl 6α-bromopenicillanate 1-oxide

6-bromopenicillanic acid

p-nitrobenzyl 6-bromopenicillanate

Downstream raw materials:

p-nitrobenzyl 2-[(3S,4R)-3-bromo-4-formylthio-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

p-nitrobenzyl 2-[(3S,4R)-4-(benzothiazol-2-yldithio)-3-bromo-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

p-nitrobenzyl 6α-bromo-2β-<<(4-nitrobenzoyl)oxy>methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide

p-nitrobenzyl 6α-bromo-2β-<<(methoxybenzoyl)oxy>methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide