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

Base Information

• Chemical Name: (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester
• CAS No.: 898831-82-8
• Molecular Formula: C₂₅H₃₆N₂O₇SSi
• Molecular Weight: 536.722
• Mol file: 898831-82-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl 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: 87.1%

(2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-hydroxybutyric acid ethyl ester (898831-81-7) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester (898831-82-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jo0606002

Reference yield:

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester (159721-18-3) → (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester (898831-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DIBAL-H / toluene; CH₂Cl₂ / 0.5 h / -78 °C

1.2: ZnCl₂; LiCl / tetrahydrofuran / 0.5 h / 0 °C

1.3: 88 percent / CH₂Cl₂; toluene; tetrahydrofuran / 2 h / 0 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

3.1: O₃ / ethyl acetate / 1.33 h / -78 °C

3.2: Me₂S / ethyl acetate / -78 - 0 °C

4.1: 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

5.1: SOCl₂ / 1 h / Heating

6.1: 87.1 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; diisobutylaluminium hydride; ozone; In dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol;

DOI:10.1021/jo0606002

Reference yield:

(3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol (898831-79-3) → (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester (898831-82-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

2.1: O₃ / ethyl acetate / 1.33 h / -78 °C

2.2: Me₂S / ethyl acetate / -78 - 0 °C

3.1: 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

4.1: SOCl₂ / 1 h / Heating

5.1: 87.1 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; ozone; In dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jo0606002

upstream raw materials:

(2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-hydroxybutyric acid ethyl ester

t-butyldimethylsiyl triflate

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

(3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol

Downstream raw materials:

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

(2S,3S)-2-(tert-butyldimethylsilanyloxy)-3-[(2,4-dimethoxybenzyl)ethoxycarbonylacetylamino]butyric acid ethyl ester

(5S,6S)-1-benzyl-5-diphenylphosphoryloxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

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