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

Base Information

• Chemical Name: (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-1-carba-2-penem-3-carboxylate
• CAS No.: 87568-67-0
• Molecular Formula: C₂₄H₂₁N₃O₁₀
• Molecular Weight: 511.445
• Mol file: 87568-67-0.mol

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

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

There total 14 articles about (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-1-carba-2-penem-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: 65.0%

p-nitrobenzyl (1'RS,3SR,4RS)-<4-allyl-3-<1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-oxoazetidin-1-yl>(triphenylphosphoranylidene)acetate (107685-91-6) → p-nitrobenzyl (1'RS,5RS,6SR)-6-<1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (87568-67-0,107794-36-5)

Guidance literature:

With ozone; In ethyl acetate; trifluoroacetic acid;

Reference yield:

p-nitrobenzyl glyoxylate (64370-35-0) → (+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-1-carba-2-penem-3-carboxylate (87568-67-0)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 2,6-dimethylpyridine; thionyl chloride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; acetone; toluene;

DOI:10.1021/ja00363a023

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)-1-carba-2-penem-3-carboxylate (87568-67-0)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 2,6-dimethylpyridine; thionyl chloride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; acetone; toluene;

DOI:10.1021/ja00363a023

upstream raw materials:

p-nitrobenzyl (1'RS,3SR,4RS)-<4-allyl-3-<1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-oxoazetidin-1-yl>(triphenylphosphoranylidene)acetate

p-nitrobenzyl glyoxylate

(1'RS,3SR,4RS)-4-allyl-1-(dimethyl-t-butylsilyl)-3-<1-(p-nitrobenzyloxycarbonyloxy)ethyl>-azetidin-2-one

(1'RS,3SR,4RS)-4-allyl-3-<1-(p-nitrobenzyloxycarbonyloxy)-ethyl>azetidin-2-one

Downstream raw materials:

(5R,6S)-3-Ethylsulfanyl-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

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

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

(5R,6S)-3-Acetoxy-3-ethanesulfonyl-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester