[2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester
• CAS No.: 886438-06-8
• Molecular Formula: C₄₇H₅₆N₂O₁₁
• Molecular Weight: 824.968
• Mol file: 886438-06-8.mol

Synonyms:[2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester

Chemical Property of [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester

There total 11 articles about [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl 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: 90.0%

{2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-[3-benzyloxy-4-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid tert-butyl ester (886437-81-6) → [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (886438-06-8)

Guidance literature:

With buffer solution; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 25 ℃; for 0.5h; pH=7;

DOI:10.1002/anie.200503983

Reference yield:

2-benzyloxy-1-[6-(tert-butyl-diphenyl-silanyloxy)-7-methyl-benzo[1,3]dioxol-4-yl]-ethanone (886437-85-0) → [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (886438-06-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: HCO₂H; triethylamine / Noyori (R,R)-catalyst / dimethylformamide / 24 h / 0 - 40 °C

1.2: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene; dimethylformamide / 24 h / 50 °C

1.3: H₂ / Pd/C / ethyl acetate / 15 h / 25 °C

2.1: acetic acid; NaCNBH₃; MgSO₄ / methanol / 4 h / 0 - 65 °C

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

4.1: 84 percent / NaH / dimethylformamide / 2 h / 0 - 25 °C

5.1: 90 percent / HCl / dioxane / 72 h / 0 - 25 °C

6.1: 85 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH₂Cl₂ / 24 h / 0 - 25 °C

7.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; buffer solution / CH₂Cl₂ / 0.5 h / 25 °C / pH 7

With hydrogenchloride; formic acid; buffer solution; tetrabutyl ammonium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; sodium cyanoborohydride; magnesium sulfate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ((1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)ruthenium chloride(I) (4-cymene); In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503983

Reference yield:

7-bromo-4-methylbenzo[d][1,3]dioxol-5-ol (351379-53-8) → [2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (886438-06-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / 12 h / 25 °C

2.1: nBuLi / toluene; tetrahydrofuran / 0.33 h / -78 °C

2.2: 80 percent / toluene; tetrahydrofuran / 50 h / -78 °C

3.1: HCO₂H; triethylamine / Noyori (R,R)-catalyst / dimethylformamide / 24 h / 0 - 40 °C

3.2: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene; dimethylformamide / 24 h / 50 °C

3.3: H₂ / Pd/C / ethyl acetate / 15 h / 25 °C

4.1: acetic acid; NaCNBH₃; MgSO₄ / methanol / 4 h / 0 - 65 °C

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

6.1: 84 percent / NaH / dimethylformamide / 2 h / 0 - 25 °C

7.1: 90 percent / HCl / dioxane / 72 h / 0 - 25 °C

8.1: 85 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH₂Cl₂ / 24 h / 0 - 25 °C

9.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; buffer solution / CH₂Cl₂ / 0.5 h / 25 °C / pH 7

With hydrogenchloride; dmap; n-butyllithium; formic acid; buffer solution; tetrabutyl ammonium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; sodium cyanoborohydride; magnesium sulfate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ((1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)ruthenium chloride(I) (4-cymene); In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200503983

upstream raw materials:

{2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-[3-benzyloxy-4-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid tert-butyl ester

7-bromo-4-methylbenzo[d][1,3]dioxol-5-ol

(7-bromo-4-methyl-benzo[1,3]dioxol-5-yloxy)-tert-butyl-diphenyl-silane

7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol

Downstream raw materials:

C₄₇H₅₁Cl₃N₂O₉Si

C₄₃H₄₃Cl₃N₂O₁₁

C₄₃H₄₁Cl₃N₂O₁₁

C₄₃H₄₁Cl₃N₂O₁₀