2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid

Base Information

• Chemical Name: 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid
• CAS No.: 886450-89-1
• Molecular Formula: C₂₈H₃₉NO₉
• Molecular Weight: 533.619

Synonyms:2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid

Chemical Property of 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid

There total 8 articles about 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid 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: 95.0%

{2,3-dihydroxy-1-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-benzyl]-propyl}-methyl-carbamic acid tert-butyl ester → 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid (886450-89-1)

Guidance literature:

With potassium permanganate; sodium periodate; sodium carbonate; In 1,4-dioxane; water; at 25 ℃; for 10h;

DOI:10.1002/anie.200503982

Reference yield:

{2-[2-azido-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,5,6-trimethoxy-4-methyl-benzyloxy}-tert-butyl-dimethyl-silane (886450-30-2) → 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid (886450-89-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / H₂ / Pd/C / ethyl acetate / 5 h / 25 °C

2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 25 °C

3: 98 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 5 h / 0 - 25 °C

4: 93 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Heating

5: aq. acetic acid / 12 h / 25 °C

6: 95 percent / KMnO₄; NaIO₄; Na₂CO₃ / H₂O; dioxane / 10 h / 25 °C

With potassium permanganate; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503982

Reference yield:

4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-but-2-en-1-ol (271578-70-2) → 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid (886450-89-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: molecular sieves 4 Angstroem; Ti(OiPr)4; tBuOOH / D-diethyl tartrate / 24 h / -20 °C

1.2: Ti(OiPr)2(N₃)2 / benzene / 5 h / 80 °C

2.1: 100 percent / TsOH*H₂O / acetone / 0.17 h / 25 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 5 h / 25 °C

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 25 °C

5.1: 98 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 5 h / 0 - 25 °C

6.1: 93 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Heating

7.1: aq. acetic acid / 12 h / 25 °C

8.1: 95 percent / KMnO₄; NaIO₄; Na₂CO₃ / H₂O; dioxane / 10 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium permanganate; sodium periodate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; Diethyl tartrate; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 1.1: Sharpless epoxidation;

DOI:10.1002/anie.200503982

upstream raw materials:

[1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2-hydroxymethyl-3,4,6-trimethoxy-5-methyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

{2-[2-azido-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,5,6-trimethoxy-4-methyl-benzyloxy}-tert-butyl-dimethyl-silane

[2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester

{1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-ethyl}-carbamic acid tert-butyl ester

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