o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate
• CAS No.: 88140-19-6
• Molecular Formula: C₃₁H₂₇N₃O₁₁
• Molecular Weight: 617.569

Synonyms:o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate

Chemical Property of o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate

There total 7 articles about o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate 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: 68.0%

(3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-hydroxymethylphenylcarbonyl)methyl-azetidin-2-one (88140-03-8) → o-nitrobenzyl-(5R*,6S*)-2-(4'-hydroxymethylphenyl)-6-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate (88140-19-6)

Guidance literature:

In xylene; for 1.5h; Heating;

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

Reference yield:

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran (17100-68-4) → o-nitrobenzyl-(5R*,6S*)-2-(4'-hydroxymethylphenyl)-6-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate (88140-19-6)

Guidance literature:

Multi-step reaction with 3 steps

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

3: 68 percent / xylene / 1.5 h / Heating

With sulfuric acid; In acetic acid; xylene;

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

Reference yield:

4-bromobenzenemethanol (873-75-6) → o-nitrobenzyl-(5R*,6S*)-2-(4'-hydroxymethylphenyl)-6-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate (88140-19-6)

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: 68 percent / xylene / 1.5 h / Heating

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

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

upstream raw materials:

(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

{(2R,3S)-2-(2-Hydroxy-ethyl)-3-[(R)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-nitro-benzyl ester

Downstream raw materials:

sodium (5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylate

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