(Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester

Base Information

• Chemical Name: (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester
• CAS No.: 93680-49-0
• Molecular Formula: C₄₃H₃₇N₂O₁₀P
• Molecular Weight: 772.748

Synonyms:

Chemical Property of (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester

There total 5 articles about (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid 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:

(Z)-3-{(R)-1-[Chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-azetidin-2-yloxy}-5-methoxy-2-oxo-pent-3-enoic acid benzyl ester (93680-48-9) + triphenylphosphine (603-35-0) → (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester (93680-49-0)

Guidance literature:

With 2,6-dimethylpyridine; In 1,4-dioxane; at 55 ℃; for 6h;

Reference yield:

p-nitrobenzyl glyoxylate (64370-35-0) → (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester (93680-49-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.75 g / triethylamine / benzene / 1.) reflux, 1 h, 2.) room temperature, 1.5 h

2: thionyl chloride, 2,6-lutidine / tetrahydrofuran / 0.25 h / 0 °C

3: 2,6-lutidine / dioxane / 6 h / 55 °C

With 2,6-dimethylpyridine; thionyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; benzene;

Reference yield:

benzyl 9-O-methylclavulanate (63612-98-6) → (Z)-5-Methoxy-3-{(R)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-yloxy}-2-oxo-pent-3-enoic acid benzyl ester (93680-49-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.1 g / selenium dioxide, t-butyl hydroperoxide / CH₂Cl₂; 2-methyl-propan-2-ol / 0.5 h / Heating

2: 1.75 g / triethylamine / benzene / 1.) reflux, 1 h, 2.) room temperature, 1.5 h

3: thionyl chloride, 2,6-lutidine / tetrahydrofuran / 0.25 h / 0 °C

4: 2,6-lutidine / dioxane / 6 h / 55 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; selenium(IV) oxide; thionyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; tert-butyl alcohol; benzene;

upstream raw materials:

(Z)-3-{(R)-1-[Chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-azetidin-2-yloxy}-5-methoxy-2-oxo-pent-3-enoic acid benzyl ester

triphenylphosphine

p-nitrobenzyl glyoxylate

benzyl 9-O-methylclavulanate

Downstream raw materials:

(R)-4-[2-Methoxy-eth-(Z)-ylidene]-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2,3-dicarboxylic acid 3-benzyl ester

4-nitrobenzyl (Z)-(6R)-3-benzyloxycarbonyl-2-(2-methoxyethylidene)-1-oxaceph-3-em-4-carboxylate

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