(Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

Base Information

• Chemical Name: (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate
• CAS No.: 1360562-71-5
• Molecular Formula: C₂₂H₂₇NO₅S
• Molecular Weight: 417.526
• Mol file: 1360562-71-5.mol

Synonyms:(Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

Chemical Property of (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

There total 4 articles about (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate 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: 80.0%

acetic acid methyl ester (79-20-9) + (S)-(+)-3-(2-phenyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide → (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate (1360562-71-5)

Guidance literature:

acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

(S)-(+)-3-(2-phenyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo202652f

Reference yield:

acetic acid methyl ester (79-20-9) + (S)-(+)-3-(2-phenyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide → (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate (1360562-71-5) + (SS,5S)-(+)-methyl N-(p-toluenesulfinyl)-5-(amino-3-oxo-7-(2-phenyl-1,3-dioxolan-2-yl)heptanoate) (1138339-13-5)

Guidance literature:

acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

(S)-(+)-3-(2-phenyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol9002948

Reference yield:

3-(2-phenyl-1,3-dioxolan-2-yl)propanal (50880-21-2) → (Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate (1360562-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo202652f

upstream raw materials:

acetic acid methyl ester

3-(2-phenyl-1,3-dioxolan-2-yl)propanal

(S)-p-toluenesulfinimide

Downstream raw materials:

(Ss,3S)-(+)-N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanal

(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

(5S,2E)-(+)-methyl (3,4-dihydro-5-phenyl-2H-pyrrol-2-yl)-but-2-enoate

C₁₅H₁₇NO₃