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.: 271578-77-9
• Molecular Formula: C₂₈H₃₉NO₉
• Molecular Weight: 533.619

Synonyms:

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: 

MSDS Files:

Useful:

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

There total 21 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:

2-hydroxy-4-methoxy-3-methylbenzaldehyde (54700-36-6) → 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid (271578-77-9)

Guidance literature:

Multi-step reaction with 21 steps

1: 100 percent / K₂CO₃ / acetonitrile / 5 h / Heating

2: 85 percent / H₂O₂; SeO₂; water / 2-methyl-propan-2-ol / 5 h / 40 °C

3: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / 12 h / 80 °C

4: 96 percent / Me₂NPh / toluene / 12 h / 210 °C

5: 87 percent / K₂CO₃ / acetonitrile / 12 h / Heating

6: TBAF / tetrahydrofuran / 1 h

7: pyridine / CH₂Cl₂ / 3 h

8: HCl; H₂O / tetrahydrofuran; propan-2-ol / 12 h

9: 96 percent / Et₂AlCl / CH₂Cl₂ / 12 h

10: 90 percent / K₂CO₃ / CHCl₃; methanol / 12 h / Heating

11: 99 percent / imidazole; DMAP / CH₂Cl₂ / 1 h

12: 94 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

13: 98 percent / (D-DET); Ti(OiPr)4; t-BuOOH / 24 h / -20 °C

14: 76 percent / Ti(OiPr)2(N₃)2 / benzene / 80 °C

15: 100 percent / p-TsOH*H₂O / acetone / 0.17 h

16: 100 percent / H₂; EtOAc / Pd/C / 5 h

17: TBAF / tetrahydrofuran / 1 h

18: NaH; nBu₄NI / tetrahydrofuran; dimethylformamide / 5 h

19: 93 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Heating

20: AcOH; water / 12 h

21: KMnO₄; NaIO₄; Na₂CO₃ / dioxane; H₂O / 10 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; potassium permanganate; sodium periodate; selenium(IV) oxide; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; ethyl acetate; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 1: Etherification / 2: oxidative cleavage / 3: Etherification / 4: p-Claisen rearrangement / 5: Etherification / 6: deprotection / 7: Acylation / 8: Hydrolysis / 9: hydroxymethylation / 10: Etherification / 11: Etherification / 12: deprotection / 13: Epoxidation / 14: acidolysis / 15: Etherification / 16: Reduction / 17: deprotection / 18: Etherification / 19: Methylation / 20: Hydrolysis / 21: oxidative cleavage;

DOI:10.1016/S0040-4039(00)00105-2

Reference yield:

(E)-4-(2,4-Dimethoxy-5-methoxymethoxy-3-methyl-phenyl)-but-2-en-1-ol → 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid (271578-77-9)

Guidance literature:

Multi-step reaction with 15 steps

1: pyridine / CH₂Cl₂ / 3 h

2: HCl; H₂O / tetrahydrofuran; propan-2-ol / 12 h

3: 96 percent / Et₂AlCl / CH₂Cl₂ / 12 h

4: 90 percent / K₂CO₃ / CHCl₃; methanol / 12 h / Heating

5: 99 percent / imidazole; DMAP / CH₂Cl₂ / 1 h

6: 94 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

7: 98 percent / (D-DET); Ti(OiPr)4; t-BuOOH / 24 h / -20 °C

8: 76 percent / Ti(OiPr)2(N₃)2 / benzene / 80 °C

9: 100 percent / p-TsOH*H₂O / acetone / 0.17 h

10: 100 percent / H₂; EtOAc / Pd/C / 5 h

11: TBAF / tetrahydrofuran / 1 h

12: NaH; nBu₄NI / tetrahydrofuran; dimethylformamide / 5 h

13: 93 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Heating

14: AcOH; water / 12 h

15: KMnO₄; NaIO₄; Na₂CO₃ / dioxane; H₂O / 10 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; potassium permanganate; sodium periodate; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; water; hydrogen; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; ethyl acetate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene; 1: Acylation / 2: Hydrolysis / 3: hydroxymethylation / 4: Etherification / 5: Etherification / 6: deprotection / 7: Epoxidation / 8: acidolysis / 9: Etherification / 10: Reduction / 11: deprotection / 12: Etherification / 13: Methylation / 14: Hydrolysis / 15: oxidative cleavage;

DOI:10.1016/S0040-4039(00)00105-2

Reference yield:

2-[4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyloxy]-4-methoxy-3-methyl-phenol (351380-00-2) → 2-(tert-butoxycarbonyl-methyl-amino)-3-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-phenyl]-propionic acid (271578-77-9)

Guidance literature:

Multi-step reaction with 19 steps

1: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / 12 h / 80 °C

2: 96 percent / Me₂NPh / toluene / 12 h / 210 °C

3: 87 percent / K₂CO₃ / acetonitrile / 12 h / Heating

4: TBAF / tetrahydrofuran / 1 h

5: pyridine / CH₂Cl₂ / 3 h

6: HCl; H₂O / tetrahydrofuran; propan-2-ol / 12 h

7: 96 percent / Et₂AlCl / CH₂Cl₂ / 12 h

8: 90 percent / K₂CO₃ / CHCl₃; methanol / 12 h / Heating

9: 99 percent / imidazole; DMAP / CH₂Cl₂ / 1 h

10: 94 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

11: 98 percent / (D-DET); Ti(OiPr)4; t-BuOOH / 24 h / -20 °C

12: 76 percent / Ti(OiPr)2(N₃)2 / benzene / 80 °C

13: 100 percent / p-TsOH*H₂O / acetone / 0.17 h

14: 100 percent / H₂; EtOAc / Pd/C / 5 h

15: TBAF / tetrahydrofuran / 1 h

16: NaH; nBu₄NI / tetrahydrofuran; dimethylformamide / 5 h

17: 93 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Heating

18: AcOH; water / 12 h

19: KMnO₄; NaIO₄; Na₂CO₃ / dioxane; H₂O / 10 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; potassium permanganate; sodium periodate; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; water; hydrogen; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; ethyl acetate; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; acetonitrile; benzene; 1: Etherification / 2: p-Claisen rearrangement / 3: Etherification / 4: deprotection / 5: Acylation / 6: Hydrolysis / 7: hydroxymethylation / 8: Etherification / 9: Etherification / 10: deprotection / 11: Epoxidation / 12: acidolysis / 13: Etherification / 14: Reduction / 15: deprotection / 16: Etherification / 17: Methylation / 18: Hydrolysis / 19: oxidative cleavage;

DOI:10.1016/S0040-4039(00)00105-2

upstream raw materials:

{(1S,2S)-2,3-Dihydroxy-1-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-benzyl]-propyl}-methyl-carbamic acid tert-butyl ester

2-hydroxy-4-methoxy-3-methylbenzaldehyde

2-[4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyloxy]-4-methoxy-3-methyl-phenol

2-[4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyloxy]-4-methoxy-3-methyl-benzaldehyde

Downstream raw materials:

[2-(1-benzyloxymethyl-5,7,8-trimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(2-formyl-3,4,6-trimethoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester

[2-(1-benzyloxymethyl-5,7,8-trimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(2-hydroxymethyl-3,4,6-trimethoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester

{2-(1-benzyloxymethyl-5,7,8-trimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-1-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-benzyl]-ethyl}-methyl-carbamic acid tert-butyl ester

{2-(1-benzyloxymethyl-4-hydroxy-5,7,8-trimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-1-[2,4,5-trimethoxy-6-(4-methoxy-benzyloxymethyl)-3-methyl-benzyl]-ethyl}-methyl-carbamic acid tert-butyl ester

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