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

Base Information

• Chemical Name: 2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3-( phenylmethoxy)-1-(phenylmethyl)-, (3R,4S)-
• CAS No.: 190007-79-5
• Molecular Formula: C30H33NO5
• Molecular Weight: 487.596
• Mol file: 190007-79-5.mol

Synonyms:

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

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-( phenylmethoxy)-1-(phenylmethyl)-, (3R,4S)-

There total 5 articles about 2-Azetidinone, 4-[(4S,5S)-2,2-dimethyl-5-[(phenylmethoxy)methyl]-1,3-dioxolan-4-yl]-3-( phenylmethoxy)-1-(phenylmethyl)-, (3R,4S)- 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: 85.0%

Benzyloxyacetyl chloride (19810-31-2) + 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-benzyloxyazetidin-2-one (190007-79-5)

Guidance literature:

With triethylamine; In dichloromethane; for 16h;

DOI:10.1039/a700815e

Reference yield:

benzyl bromide (100-39-0) + (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one (190007-78-4) → (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-benzyloxyazetidin-2-one (190007-79-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -20 ℃;

DOI:10.1039/a700815e

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-benzyloxyazetidin-2-one (190007-79-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 16 h

2: aq. LiOH, H₂O₂ / tetrahydrofuran / 3 h / 0 °C

3: NaH / dimethylformamide / -20 °C

With lithium hydroxide; dihydrogen peroxide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/a700815e

upstream raw materials:

Benzyloxyacetyl chloride

benzyl bromide

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

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

Downstream raw materials:

(+)-(3R,4R)-cis-1-benzyl-3-benzyloxy-4-formyl-2-azetidinone

(3R,4S)-1-Benzyl-3-benzyloxy-4-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one

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

(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione