2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3- hydroxy-1-(phenylmethyl)-, (3R,4R)-

Base Information

• Chemical Name: 2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3- hydroxy-1-(phenylmethyl)-, (3R,4R)-
• CAS No.: 190007-78-4
• Molecular Formula: C23H27NO5
• Molecular Weight: 397.471
• Mol file: 190007-78-4.mol

Synonyms:

Chemical Property of 2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3- hydroxy-1-(phenylmethyl)-, (3R,4R)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3- hydroxy-1-(phenylmethyl)-, (3R,4R)-

There total 3 articles about 2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3- hydroxy-1-(phenylmethyl)-, (3R,4R)- 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: 95.0%

(3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one (213480-19-4) → (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one (190007-78-4)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1021/jo980354x

Reference yield:

Benzyl-[1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine → (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one (190007-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 7.91 g / triethylamine / CH₂Cl₂ / 0 - 20 °C

2: 95 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

With lithium hydroxide; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: Cycloaddition / 2: Deacetylation;

DOI:10.1021/jo980354x

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one (190007-78-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 4A MS / CH₂Cl₂ / 1 h / 0 °C

2: 7.91 g / triethylamine / CH₂Cl₂ / 0 - 20 °C

3: 95 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

With lithium hydroxide; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: Condensation / 2: Cycloaddition / 3: Deacetylation;

DOI:10.1021/jo980354x

upstream raw materials:

(3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

Downstream raw materials:

(3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-benzyloxyazetidin-2-one

(S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester

(S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-phenyl-propionic acid benzyl ester

(S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-4-methyl-pentanoic acid benzyl ester