(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone

Base Information

• Chemical Name: (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone
• CAS No.: 277757-28-5
• Molecular Formula: C₁₉H₂₃NO₇
• Molecular Weight: 377.394
• Mol file: 277757-28-5.mol

Synonyms:(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone

Chemical Property of (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone

There total 3 articles about (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone 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: 72.0%

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-87-0) + propynoic acid methyl ester (922-67-8) → (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone (277757-28-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo991641j

Reference yield:

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine (103239-04-9) → (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone (277757-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 95 percent / sodium methoxide / methanol / 0.33 h / 20 °C

3: 72 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With sodium methylate; triethylamine; In methanol; dichloromethane; 1: Staudinger reaction / 2: Deacetylation / 3: Addition;

DOI:10.1021/jo991641j

Reference yield:

(3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (103174-02-3) → (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone (277757-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / sodium methoxide / methanol / 0.33 h / 20 °C

2: 72 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With sodium methylate; triethylamine; In methanol; dichloromethane; 1: Deacetylation / 2: Addition;

DOI:10.1021/jo991641j

upstream raw materials:

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

propynoic acid methyl ester

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine

(3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Downstream raw materials:

(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

(+)-(3R,4R)-3-(2-carboxymethyl-1-ethenyloxy)-4-formyl-1-(p-methoxyphenyl)-2-azetidinone