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

Base Information

• Chemical Name: diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate
• CAS No.: 171754-12-4
• Molecular Formula: C₂₃H₂₃NO₅
• Molecular Weight: 393.439
• Mol file: 171754-12-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-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: 86.0%

(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 (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate (171754-12-4)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane;

DOI:10.1016/0040-4039(95)01703-K

Reference yield: 51.0%

(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 (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate (171754-11-3) + 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)

Guidance literature:

With methanesulfonic acid; In dichloromethane; at -20 - -15 ℃; for 1h;

DOI:10.1016/0040-4039(95)01703-K

Reference yield:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone (158150-46-0) → 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)

Guidance literature:

Multi-step reaction with 2 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

With dirhodium tetraacetate; sodium methylate; In methanol; dichloromethane;

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

upstream raw materials:

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

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

1,1-Diphenylmethanol

4(R)-<1-buten-3(S)-yl>-3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxoazetidine

Downstream raw materials:

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