(+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate

Base Information

• Chemical Name: (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate
• CAS No.: 87638-51-5
• Molecular Formula: C₃₀H₂₇N₃O₁₀S
• Molecular Weight: 621.624
• Mol file: 87638-51-5.mol

Synonyms:(+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate

Chemical Property of (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate

There total 10 articles about (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-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:

(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-98-4) → (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate (87638-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / toluene / 2 h / Heating

2: SOCl₂, pyridine / tetrahydrofuran / -20 °C

3: 2,6-lutidine / dioxane / 1.) room temperature, 24 h, 2.) 50 deg C, 4 h

4: p-TsOH / tetrahydrofuran / 1 h

5: acetone / 6 h / Ambient temperature

6: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; thionyl chloride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00363a023

Reference yield:

p-nitrobenzyl glyoxylate (64370-35-0) → (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate (87638-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / toluene / 2 h / Heating

2: SOCl₂, pyridine / tetrahydrofuran / -20 °C

3: 2,6-lutidine / dioxane / 1.) room temperature, 24 h, 2.) 50 deg C, 4 h

4: p-TsOH / tetrahydrofuran / 1 h

5: acetone / 6 h / Ambient temperature

6: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; thionyl chloride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00363a023

Reference yield:

(p-Nitrobenzyloxycarbonylmethylene)triphenylphosphorane (63760-39-4) → (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate (87638-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / CH₂Cl₂ / 1 h / Heating

2: 2.) NaBH₄, 3.) Et₃N, NaI, K₂CO₃

With sodium tetrahydroborate; potassium carbonate; triethylamine; sodium iodide; In dichloromethane;

DOI:10.1021/ja00363a023

upstream raw materials:

thiophenol

(+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-1-carba-2-penem-3-carboxylate

(+/-)-3(R*)-(1(S*)((((p-nitrobenzyl)oxy)carbonyl)oxy)ethyl)-4(R*)-(3-(((p-nitrobenzyl)oxy)carbonyl)-2-propenyl)azetidin-2-one

benzenesulfenyl chloride