(+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde

Base Information

• Chemical Name: (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde
• CAS No.: 251480-03-2
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.262
• Mol file: 251480-03-2.mol

Synonyms:(+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde

Chemical Property of (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde

There total 5 articles about (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde 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:

(3R,4S)-1-But-3-ynyl-4-((S)-1,2-dihydroxy-ethyl)-3-phenoxy-azetidin-2-one → (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde (251480-03-2)

Guidance literature:

With sodium periodate; In methanol; water; at 20 ℃;

DOI:10.1016/S0040-4039(00)00006-X

Reference yield:

But-3-ynyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-amine → (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde (251480-03-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / triethylamine / CH₂Cl₂ / 16 h / 20 °C

2: p-TsOH*H₂O / tetrahydrofuran / 2 h / Heating

3: 0.70 g / sodium periodate; sodium hydrogen carbonate / CH₂Cl₂ / 2 h / 20 °C

With sodium periodate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; 1: Staudinger reaction;

DOI:10.1021/jo005715z

Reference yield:

(+)-(3R,4S)-1-(3-butynyl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenoxy-2-azetidinone (331258-73-2) → (+)-(2R,3R)-1-(3-butynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde (251480-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / tetrahydrofuran / 2 h / Heating

2: 0.70 g / sodium periodate; sodium hydrogen carbonate / CH₂Cl₂ / 2 h / 20 °C

With sodium periodate; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo005715z

upstream raw materials:

Phenoxyacetyl chloride

(+)-(3R,4S)-1-(3-butynyl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenoxy-2-azetidinone

Downstream raw materials:

(3R,4S)-1-(3-butynyl)-4-[(R)-1-hydroxy-2-methylidene-3-oxo-butyl]-3-phenoxy-2-azetidinone

C₁₅H₁₆N₂O₃