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

Base Information

• Chemical Name: (3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• CAS No.: 115828-84-7
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 115828-84-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 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: 70.0%

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-87-0) + allyl bromide (106-95-6) → (3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-84-7)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; water; at 20 ℃; for 20h;

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)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (103174-02-3) + allyl bromide (106-95-6) → (3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-84-7)

Guidance literature:

(3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one; With sodium methylate; In methanol; at 20 ℃;

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one; allyl bromide; With sodium hydroxide; tetrabutylammomium bromide;

DOI:10.1016/S0040-4039(99)01013-8

Reference yield:

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine (103239-04-9) → (3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-84-7)

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

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

DOI:10.1021/jo991641j

upstream raw materials:

allyloxyacetyl chloride

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-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(2-iodo-ethoxy)-1-(4-methoxy-phenyl)-azetidin-2-one

(3R,4S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(2-hydroxy-ethoxy)-1-(4-methoxy-phenyl)-azetidin-2-one

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

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