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

Base Information

• Chemical Name: (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone
• CAS No.: 277757-84-3
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32
• Mol file: 277757-84-3.mol

Synonyms:(+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone

Chemical Property of (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone

There total 4 articles about (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-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: 100.0%

(3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-84-7) → (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone (277757-84-3)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; for 2h; Heating;

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-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone (277757-84-3)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 70 percent / sodium hydroxide; tetrabutyl ammonium iodide / CH₂Cl₂; H₂O / 20 h / 20 °C

4: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

With sodium hydroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Staudinger reaction / 2: Deacetylation / 3: Alkylation / 4: Hydrolysis;

DOI:10.1021/jo991641j

Reference yield:

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-87-0) → (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone (277757-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / sodium hydroxide; tetrabutyl ammonium iodide / CH₂Cl₂; H₂O / 20 h / 20 °C

2: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; 1: Alkylation / 2: Hydrolysis;

DOI:10.1021/jo991641j

upstream raw materials:

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

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

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

(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)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

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