diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Base Information

• Chemical Name: diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate
• CAS No.: 147118-02-3
• Molecular Formula: C₃₅H₃₂NO₈P
• Molecular Weight: 625.615
• Mol file: 147118-02-3.mol

Synonyms:diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Chemical Property of diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

There total 13 articles about diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-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: 75.0%

chlorophosphoric acid diphenyl ester (2524-64-3) + diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate (171754-12-4) → diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (147118-02-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 1h;

DOI:10.1016/S0040-4020(96)01093-9

Reference yield:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone (158150-46-0) → diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (147118-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / sodium methoxide / methanol / 1 h / 20 °C

2: 86 percent / rhodium(II) acetate dimer / CH₂Cl₂ / 0.33 h / Ambient temperature; other reagents: p-toluenesulfonic acid monohydrate, methanesulfonic acid, sulfuric acid, perchloric acid, trifluoroborane etherate, rhodium(II) octanoate dimer

3: 75 percent / diisopropylethylamine / acetonitrile / 1 h

With dirhodium tetraacetate; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(96)01093-9

Reference yield:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxo-3-phenyliodoniopropyl>-2-azetidinone (187280-57-5,158150-43-7) → diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (147118-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / rhodium(II) acetate dimer / CH₂Cl₂ / 0.33 h / Ambient temperature; other reagents: p-toluenesulfonic acid monohydrate, methanesulfonic acid, sulfuric acid, perchloric acid, trifluoroborane etherate, rhodium(II) octanoate dimer

2: 75 percent / diisopropylethylamine / acetonitrile / 1 h

With dirhodium tetraacetate; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(96)01093-9

upstream raw materials:

chlorophosphoric acid diphenyl ester

diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate

diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxo-3-phenyliodoniopropyl>-2-azetidinone

Downstream raw materials:

C₃₉H₅₂N₄O₁₀S₂

diphenylmethyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(3S,5S)-1-(tert-butoxycarbonyl)-5-[N-sulfamoyl-N-(tert-butoxycarbonyl)aminomethyl]pyrrolidin-3-yl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

C₃₈H₅₀N₄O₁₀S₂