benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate

Base Information

• Chemical Name: benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate
• CAS No.: 1384468-52-3
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293
• Mol file: 1384468-52-3.mol

Synonyms:benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate

Chemical Property of benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate

There total 3 articles about benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate 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%

isobutyraldehyde (78-84-2) + benzyl (E)-β-nitroacrylate → benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate (1384468-52-3)

Guidance literature:

With L-phenylalanine; L-Phenylalanine lithium salt; In dichloromethane; at 25 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c2ob25413a

Reference yield:

isobutyraldehyde (78-84-2) + benzyl (E)-β-nitroacrylate → benzyl (R)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate + benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate (1384468-52-3)

Guidance literature:

With L-Phenylalanine lithium salt; In dichloromethane; at 25 ℃; for 19h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c2ob25413a

Reference yield:

benzyl 2-hydroxy-3-nitropropionate → benzyl (S)-3,3-dimethyl-2-nitromethyl-4-oxobutyrate (1384468-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / -20 °C / Inert atmosphere

2: L-phenylalanine; L-Phenylalanine lithium salt / dichloromethane / 24 h / 25 °C

With L-phenylalanine; methanesulfonyl chloride; triethylamine; L-Phenylalanine lithium salt; In dichloromethane; 2: Michael addition;

DOI:10.1039/c2ob25413a

upstream raw materials:

isobutyraldehyde

Downstream raw materials:

(S)-4,4-dimethylpyrrolidine-3-carboxylic acid

(S)-N-(2-nitrophenylsulfonyl)-4,4-dimethylpyrrolidine-3-carboxylic acid

benzyl (S)-3-[1,3]dioxolan-2-yl-2-nitromethyl-3-methylbutyrate