Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine

Base Information

• Chemical Name: Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine
• CAS No.: 153472-19-6
• Molecular Formula: C₂₁H₂₄N₂O₂
• Molecular Weight: 336.434
• Mol file: 153472-19-6.mol

Synonyms:Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine

Chemical Property of Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine

There total 2 articles about Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine 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:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) → Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine (153472-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBALH / toluene / 3 h / -78 °C

2: toluene / 20 h / Ambient temperature

With diisobutylaluminium hydride; In toluene;

DOI:10.1021/jo00083a042

Reference yield:

(4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde (122137-20-6) + benzylamine (100-46-9) → Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine (153472-19-6)

Guidance literature:

In toluene; for 20h; Yield given; Ambient temperature;

DOI:10.1021/jo00083a042

Reference yield: 61.0%

Phenoxyacetyl chloride (701-99-5) + Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine (153472-19-6) → (4S,5S,3'R,4'S)-2,2-Dimethyl-4,5-bis(1'-benzyl-2'-oxo-3'-phenoxyazetidin-4'-yl)-1,3-dioxolane (153472-22-1)

Guidance literature:

With triethylamine; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1021/jo00083a042

upstream raw materials:

(4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde

benzylamine

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Downstream raw materials:

C₃₉H₄₀N₂O₆

(4S,5S,3'R,4'S)-2,2-Dimethyl-4,5-bis(1'-benzyl-2'-oxo-3'-phenoxyazetidin-4'-yl)-1,3-dioxolane

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

(3R,4R)-N-Benzyl-3-phenoxy-4-formylazetidin-2-one