(-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester

Base Information

• Chemical Name: (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester
• CAS No.: 1281895-24-6
• Molecular Formula: C₂₃H₃₄N₂O₉
• Molecular Weight: 482.531
• Mol file: 1281895-24-6.mol

Synonyms:(-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester

Chemical Property of (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester

There total 4 articles about (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester 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:

di-tert-butyl-diazodicarboxylate (870-50-8) + methyl 3-(3,4-dimethoxyphenyl)-2-methyl-3-oxopropanoate (168165-94-4) → (+)-1-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-44-0) + (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-24-6)

Guidance literature:

With europium(III) trifluoromethanesulfonate; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine; In acetonitrile; at 20 ℃; for 1.5h; Reagent/catalyst; Time; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol400136y

Reference yield:

methyl 3-(3,4-dimethoxyphenyl)-2-methyl-3-oxopropanoate (168165-94-4) + di-tert-butyl (E)-azodicarboxylate (870-50-8) → (+)-1-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-44-0) + (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-24-6)

Guidance literature:

With (R)-3,3'-dibromo-1,1'-bi-2-naphthol; lithium hydroxide; In diethyl ether; at -30 ℃; for 24h; Overall yield = 95 %; Overall yield = 229.6 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2017.08.015

Reference yield:

1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → (+)-1-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-44-0) + (-)-1-[(1R)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 5 h / Reflux

2: potassium carbonate / acetone / 24 h / 40 °C

3: europium(III) trifluoromethanesulfonate; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine / acetonitrile / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

With sodium hydride; potassium carbonate; europium(III) trifluoromethanesulfonate; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine; In tetrahydrofuran; acetone; acetonitrile; mineral oil; 3: |Michael Addition;

DOI:10.1021/ol400136y

upstream raw materials:

1-(3,4-dimethoxyphenyl)ethanone

methyl 3-(3,4-dimethoxyphenyl)-3-oxopropionate

di-tert-butyl-diazodicarboxylate

methyl 3-(3,4-dimethoxyphenyl)-2-methyl-3-oxopropanoate