(2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester

Base Information

• Chemical Name: (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester
• CAS No.: 930579-53-6
• Molecular Formula: C₂₃H₃₅NO₄Si
• Molecular Weight: 417.621
• Mol file: 930579-53-6.mol

Synonyms:(2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester

Chemical Property of (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester

There total 5 articles about (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester 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:

(5S,6S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-piperidine-2,4-dione → (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester (930579-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.41 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

2: 90.7 percent / Pd[P(o-Tol)3]2Cl₂ / tetrahydrofuran / 1 h / 20 °C

With triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2006.12.055

Reference yield:

(2S,3S)-3-Benzylamino-2-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester → (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester (930579-53-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.87 g / diisopropylethylamine / CH₂Cl₂ / 10 h / 20 °C

2: NaOEt / ethanol / 0.75 h / cooling

3: H₂O / acetonitrile / 2 h / Heating

4: 2.41 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

5: 90.7 percent / Pd[P(o-Tol)3]2Cl₂ / tetrahydrofuran / 1 h / 20 °C

With water; sodium ethanolate; triethylamine; N-ethyl-N,N-diisopropylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2006.12.055

Reference yield:

(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester (930579-51-4) → (2S,3S)-3-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]propionic acid methyl ester (930579-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOEt / ethanol / 0.75 h / cooling

2: H₂O / acetonitrile / 2 h / Heating

3: 2.41 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

4: 90.7 percent / Pd[P(o-Tol)3]2Cl₂ / tetrahydrofuran / 1 h / 20 °C

With water; sodium ethanolate; triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2006.12.055

upstream raw materials:

(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

(2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

Downstream raw materials:

(3S,6S)-2-benzyl-3-methyl-2,3,5,6,7,7a-hexahydro[2]pyrindin-1-one

acetic acid (2S,3S)-1-benzyl-2-methyl-6-oxo-4-(3-oxopropyl)-1,2,3,6-tetrahydropyridin-3-yl ester

acetic acid (2S,3S)-1-benzyl-4-(3-iodo-propyl)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-3-yl ester

(1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester