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

Base Information

• Chemical Name: [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester
• CAS No.: 107685-90-5
• Molecular Formula: C₄₂H₃₆N₃O₁₁P
• Molecular Weight: 789.735

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

Chemical Property of [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

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Technology Process of [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

There total 5 articles about [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester 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:

{(2R,3R)-2-(2,2-Dimethoxy-ethyl)-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (87568-66-9) → [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (107685-90-5)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; for 1h;

DOI:10.1021/ja00363a023

Reference yield:

p-nitrobenzyl glyoxylate (64370-35-0) → [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (107685-90-5)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ja00363a023

Reference yield:

(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-98-4) → [(3R,4R)-3-[(S)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (107685-90-5)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ja00363a023

upstream raw materials:

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

p-nitrobenzyl glyoxylate

(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

(+/-)-1-(hydroxy(((p-nitrobenzyl)oxy)carbonyl)methyl)-4(R*)-(2,2-dimethoxyethyl)-3(R*)-(1(S*)-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethyl)azetidin-2-one

Downstream raw materials:

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

(+/-)-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

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