(2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester

Base Information

• Chemical Name: (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester
• CAS No.: 881206-28-6
• Molecular Formula: C₁₈H₂₅NO₇
• Molecular Weight: 367.399
• Mol file: 881206-28-6.mol

Synonyms:(2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester

Chemical Property of (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester

There total 4 articles about (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-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: 85.0%

(2R,3R)-4-Amino-2,3-dihydroxy-2-methyl-butyric acid ethyl ester; hydrochloride + 3,4-dimethoxy-trans-cinnamic acid (14737-89-4) → (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester (881206-28-6)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.11.051

Reference yield:

ethyl 4-[N-(t-butyloxycarbonyl)amino]-2,3-dihydroxy-2-methyl-butanoate (881206-24-2) → (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester (881206-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / diethyl ether

2: 85 percent / triethylamine; benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-) / dimethylformamide

With hydrogenchloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.11.051

Reference yield:

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → (2R,3R)-4-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester (881206-28-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 3 h / -78 °C

2.1: AD-mix-β; methane sulfonamide / H2O; 2-methyl-propan-2-ol / 0 - 20 °C

3.1: HCl / diethyl ether

4.1: 85 percent / triethylamine; benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-) / dimethylformamide

With hydrogenchloride; n-butyllithium; methanesulfonamide; AD-mix-β; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2005.11.051

upstream raw materials:

3,4-dimethoxy-trans-cinnamic acid

ethyl 4-[N-(t-butyloxycarbonyl)amino]-2,3-dihydroxy-2-methyl-butanoate

ethyl 2-diethoxyphosphorylpropionate

ethyl (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoate

Downstream raw materials:

(4R,5R)-5-{[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-methyl}-2,2,4-trimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

3,4-dimethoxy-trans-cinnamic acid