(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one
• CAS No.: 88140-04-9
• Molecular Formula: C₅₀H₄₄N₃O₁₄PS
• Molecular Weight: 973.951

Synonyms:(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one

Chemical Property of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one

There total 7 articles about (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-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: 72.4%

methanesulfonyl chloride (124-63-0) + (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-hydroxymethylphenylcarbonyl)methyl-azetidin-2-one (88140-03-8) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one (88140-04-9)

Guidance literature:

With triethylamine; In dichloromethane; 0 deg C, 0.5 h, RT, overnight;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran (17100-68-4) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one (88140-04-9)

Guidance literature:

Multi-step reaction with 3 steps

2: 78 percent / 10percent H₂SO₄ aq. / acetic acid / 0.5 h / Ambient temperature

3: 72.4 percent / Et₃N / CH₂Cl₂ / 0 deg C, 0.5 h, RT, overnight

With sulfuric acid; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

4-bromobenzenemethanol (873-75-6) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-methylsulfonyloxymethylphenylcarbonyl)methyl-azetidin-2-one (88140-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / p-TsOH / CH₂Cl₂ / 2 h / Ambient temperature

3: 78 percent / 10percent H₂SO₄ aq. / acetic acid / 0.5 h / Ambient temperature

4: 72.4 percent / Et₃N / CH₂Cl₂ / 0 deg C, 0.5 h, RT, overnight

With sulfuric acid; toluene-4-sulfonic acid; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(01)92147-7

upstream raw materials:

methanesulfonyl chloride

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-hydroxymethylphenylcarbonyl)methyl-azetidin-2-one

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

4-bromobenzenemethanol

Downstream raw materials:

(5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

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