p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate

Base Information

• Chemical Name: p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate
• CAS No.: 71367-56-1
• Molecular Formula: C₂₂H₁₉N₃O₈S₄
• Molecular Weight: 581.672
• Mol file: 71367-56-1.mol

Synonyms:p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate

Chemical Property of p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate

There total 4 articles about p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate 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-((R)-2-benzothiazol-2-yldisulfanyl-4-oxo-azetidin-1-yl)-3-oxo-butyric acid 4-nitro-benzyl ester (71355-65-2) + methanesulfonyl chloride (124-63-0) → p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate (71367-56-1)

Guidance literature:

With triethylamine; In dichloromethane; at -15 ℃;

DOI:10.1039/c39790000665

Reference yield:

penicillanic acid 4-nitro-benzyl ester (69388-89-2) → p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate (71367-56-1)

Guidance literature:

Multi-step reaction with 4 steps

1: MCPBA

2: toluene / 4 h / Heating

3: O₃ / CH₂Cl₂ / -78 °C

4: Et₃N / CH₂Cl₂ / -15 °C

With ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;

DOI:10.1039/c39790000665

Reference yield:

1β-oxo-1λ4-penicillanic acid 4-nitro-benzyl ester (72554-59-7) → p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-methylsulphonyloxy but-2-enoate (71367-56-1)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 4 h / Heating

2: O₃ / CH₂Cl₂ / -78 °C

3: Et₃N / CH₂Cl₂ / -15 °C

With ozone; triethylamine; In dichloromethane; toluene;

DOI:10.1039/c39790000665

upstream raw materials:

2-((R)-2-benzothiazol-2-yldisulfanyl-4-oxo-azetidin-1-yl)-3-oxo-butyric acid 4-nitro-benzyl ester

methanesulfonyl chloride

penicillanic acid 4-nitro-benzyl ester

1β-oxo-1λ⁴-penicillanic acid 4-nitro-benzyl ester

Downstream raw materials:

p-nitrobenzyl-2-(4R-ethylsulphenamoyl-2-oxo-1-azetidinyl)-3-methylsulphonyloxybut-2-enoate

p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-ethylamino but-2-enoate

p-nitrobenzyl-<4R-(2-benzthiazolyldithio)-2-oxo-1-azetidinyl>-3-anilino but-2-enoate

(6R)-3-methyl-2-phenyl-4-(p-nitrobenzyloxycarbonyl)-2-azacephem