(4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone

Base Information

• Chemical Name: (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone
• CAS No.: 139308-01-3
• Molecular Formula: C₂₀H₂₉NO₆
• Molecular Weight: 379.453
• Mol file: 139308-01-3.mol

Synonyms:(4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone

Chemical Property of (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone

There total 8 articles about (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-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: 96.0%

(4S,5S)-4,5-dimethoxymethyl-2-(N-p-methoxyphenyl)iminomethyl-2-methyl-1,3-dioxolane (146726-49-0) + Ethyl isobutyrate (97-62-1) → (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone (139308-01-3)

Guidance literature:

With lithium diisopropyl amide; Mechanism; Product distribution; multistep reaction; other metal ester enolates; enantioselectivity;

DOI:10.1016/0040-4020(92)80013-6

Reference yield: 85.0%

(3R,4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3-methyl-2-azetidinone (148018-82-0) + methyl iodide (74-88-4) → (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone (139308-01-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1) -78 deg C, 2) RT;

DOI:10.1016/S0040-4039(00)91781-7

Reference yield:

(-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol (50622-10-1) → (4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone (139308-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / p-toluenesulfonic acid, molecular sieves 4 Angstroem / benzene / 4 h / Heating

2: 1.) (COCl)2, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) r.t., 8 h

3: 88 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 16 h / Ambient temperature

With oxalyl dichloride; 4 A molecular sieve; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene;

DOI:10.1016/0040-4020(92)80013-6

upstream raw materials:

(4S,5S)-4,5-Dimethoxymethyl-2-(N-p-methoxyphenyl)iminomethyl-2-methyl-1,3-dioxolane

Ethyl isobutyrate

(4S,5S)-4,5-dimethoxymethyl-2-(N-p-methoxyphenyl)iminomethyl-2-methyl-1,3-dioxolane

(3R,4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3-methyl-2-azetidinone