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

Base Information

• Chemical Name: {(2R,3S)-2-(2,2-Dimethoxy-ethyl)-3-[(S)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-nitro-benzyl ester
• CAS No.: 72679-67-5
• Molecular Formula: C₄₄H₄₂N₃O₁₂P
• Molecular Weight: 835.804

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

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

Chemical Property:

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

There total 6 articles about {(2R,3S)-2-(2,2-Dimethoxy-ethyl)-3-[(S)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-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: 74.0%

Chloro-{(2R,3S)-2-(2,2-dimethoxy-ethyl)-3-[(S)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 2-nitro-benzyl ester + triphenylphosphine (603-35-0) → {(2R,3S)-2-(2,2-Dimethoxy-ethyl)-3-[(S)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-nitro-benzyl ester (72679-67-5)

Guidance literature:

With 2,6-dimethylpyridine; In 1,4-dioxane; Ambient temperature;

DOI:10.1021/ja00526a048

Reference yield:

o-nitrobenzyl chloroformate (42854-99-9) → {(2R,3S)-2-(2,2-Dimethoxy-ethyl)-3-[(S)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-nitro-benzyl ester (72679-67-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

2: 69 percent / molecular sieves / dimethylformamide; toluene / 24 h / Ambient temperature

3: SO₂Cl₂, 2,6-lutidine / tetrahydrofuran / 0.5 h / -20 °C

4: 74 percent / 2,6-lutidine / dioxane / Ambient temperature

With 2,6-dimethylpyridine; dmap; sulfuryl dichloride; molecular sieve; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00526a048

Reference yield:

trans-4-(2',2'-dimethoxyethyl)-3-(1'-o-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (72679-64-2) → {(2R,3S)-2-(2,2-Dimethoxy-ethyl)-3-[(S)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-nitro-benzyl ester (72679-67-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / molecular sieves / dimethylformamide; toluene / 24 h / Ambient temperature

2: SO₂Cl₂, 2,6-lutidine / tetrahydrofuran / 0.5 h / -20 °C

3: 74 percent / 2,6-lutidine / dioxane / Ambient temperature

With 2,6-dimethylpyridine; sulfuryl dichloride; molecular sieve; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00526a048

upstream raw materials:

triphenylphosphine

o-nitrobenzyl chloroformate

trans-4-(2',2'-dimethoxyethyl)-3-(1'-o-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

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

Downstream raw materials:

o-nitrobenzyl 6-((8S*)-o-nitrobenzyloxycarbonyloxyethyl)-1-carba-2-penem-3-carboxylate

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