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

Base Information

• Chemical Name: (3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol
• CAS No.: 898831-79-3
• Molecular Formula: C₁₈H₂₀N₂O₅S
• Molecular Weight: 376.433
• Mol file: 898831-79-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol 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: 88.0%

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester (159721-18-3) + vinylmagnesium chloride (3536-96-7) → (3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol (898831-79-3)

Guidance literature:

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

vinylmagnesium chloride; With lithium chloride; zinc(II) chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

In tetrahydrofuran; dichloromethane; toluene; at 0 ℃; for 2h;

DOI:10.1021/jo0606002

Reference yield:

N-(2-nitrobenzenesulfonyl)-(S)-alanine methyl ester (215056-53-4) → (3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol (898831-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 56.3 g / K₂CO₃ / dimethylformamide / 12 h / 20 °C

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

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

2.3: 88 percent / CH₂Cl₂; toluene; tetrahydrofuran / 2 h / 0 °C

With diisobutylaluminium hydride; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0606002

Reference yield: 100.0%

(3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol (898831-79-3) + t-butyldimethylsiyl triflate (69739-34-0) → (3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]-3-(tert-butyldimethylsilanyloxy)pent-1-ene (898831-80-6)

Guidance literature:

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

DOI:10.1021/jo0606002

upstream raw materials:

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

vinylmagnesium chloride

N-(2-nitrobenzenesulfonyl)-(S)-alanine methyl ester

Downstream raw materials:

(3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]-3-(tert-butyldimethylsilanyloxy)pent-1-ene

(1S,2R)-N-benzyl-N-(2-hydroxy-1-methylbut-3-enyl)acrylamide

(-)-(5R,6S)-1-benzyl-5-hydroxy-6-methyl-5,6-dihydropyridin-2(1H)-one

(5R,6S)-1-benzyl-5,6-dihydro-6-methyl-5-diphenylphosphoryloxy-1H-pyridine-2-one