(5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one

Base Information

• Chemical Name: (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one
• CAS No.: 930579-52-5
• Molecular Formula: C₂₀H₂₈F₃NO₅SSi
• Molecular Weight: 479.593
• Mol file: 930579-52-5.mol

Synonyms:(5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one

Chemical Property of (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one

There total 11 articles about (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-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:

(5S,6S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-piperidine-2,4-dione + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one (930579-52-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0606002

Reference yield:

(2S,3S)-3-Benzylamino-2-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester → (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one (930579-52-5)

Guidance literature:

Multi-step reaction with 4 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

With water; sodium ethanolate; triethylamine; N-ethyl-N,N-diisopropylamine; In 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) → (5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one (930579-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOEt / ethanol / 0.75 h / cooling

2: H₂O / acetonitrile / 2 h / Heating

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

With water; sodium ethanolate; triethylamine; In ethanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2006.12.055

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

(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

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl 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

(5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-4-(3-hydroxypropyl)-6-methyl-5,6-dihydro-1H-pyridin-2-one