methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate

Base Information

• Chemical Name: methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate
• CAS No.: 146848-86-4
• Molecular Formula: C₁₉H₁₉NO₅
• Molecular Weight: 341.364
• Mol file: 146848-86-4.mol

Synonyms:methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate

Chemical Property of methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate

There total 14 articles about methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate 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: 42.0%

methanol (67-56-1) + (+/-)-cis-1-benzoyl-3-acetoxy-4-phenylazetidin-2-one (146924-93-8) → (3S,4R)-1-Benzoyl-3-hydroxy-4-phenyl-azetidin-2-one + methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate (146848-86-4)

Guidance literature:

In various solvent(s); at 50 ℃; for 48h; Pseudomonas sp. lipase AK;

DOI:10.1021/jo00057a018

Reference yield:

N-(methoxy(phenyl)methyl)benzamide (10387-93-6) → methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate (146848-86-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 66 percent / 120 °C / 0.5 Torr

2.1: NaHMDS / tetrahydrofuran / -78 - 20 °C

2.2: SiO₂

3.1: 82 percent / aq. HCl / dioxane / 0.67 h / 50 °C

4.1: 95 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

5.1: NaIO₄; RuCl₃ / acetonitrile; CCl₄; H₂O / 6 h

6.1: 36 mg / diethyl ether; methanol; hexane / 0.5 h / 20 °C

With pyridine; hydrogenchloride; dmap; ruthenium trichloride; sodium periodate; sodium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; acetonitrile;

DOI:10.1021/ol035554w

Reference yield:

benzamide (55-21-0,27208-38-4) → methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate (146848-86-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 57 percent / toluene / 24 h / γ-Irradiation

2.1: 88 percent / methanol / 20 °C

3.1: 66 percent / 120 °C / 0.5 Torr

4.1: NaHMDS / tetrahydrofuran / -78 - 20 °C

4.2: SiO₂

5.1: 82 percent / aq. HCl / dioxane / 0.67 h / 50 °C

6.1: 95 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

7.1: NaIO₄; RuCl₃ / acetonitrile; CCl₄; H₂O / 6 h

8.1: 36 mg / diethyl ether; methanol; hexane / 0.5 h / 20 °C

With pyridine; hydrogenchloride; dmap; ruthenium trichloride; sodium periodate; sodium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/ol035554w

upstream raw materials:

methanol

(+/-)-cis-1-benzoyl-3-acetoxy-4-phenylazetidin-2-one

diazomethyl-trimethyl-silane

(2R,3S)-N-benzoyl-O-acetyl-3-phenylisoserine

Downstream raw materials:

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

(2R,3S)-N-benzoyl-3-phenylisoserine

Refernces

• 1、 Brieva, Rosario,Crich, Joyce Z.,Sih, Charles J.. "Chemoenzymatic Synthesis of the C-13 Side Chain of Taxol: Optically Active 3-Hydroxy-4-phenyl β-Lactam Derivatives". . p. 1068 - 1075. Retrieved 2007/10/02.