{2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 866110-69-2
• Molecular Formula: C₅₄H₆₈N₂O₁₁Si
• Molecular Weight: 949.226

Synonyms:{2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

There total 16 articles about {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl 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:

{2-(8-allyloxy-1-allyloxymethyl-3-hydroxymethyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester (866110-82-9) → {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester (866110-69-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ja0535918

Reference yield:

(5-benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-methanol → {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester (866110-69-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: PPh₃; I₂; imidazole / CH₂Cl₂ / 0.5 h / 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.75 h / -78 °C

2.2: 4.73 g / tetrahydrofuran / 4 h / -78 °C

3.1: H₂ / Pd/BaSO₄ / tetrahydrofuran / 24 h / 760 Torr

4.1: trifluoroacetic acid / CH₂Cl₂ / 12 h / 20 °C

5.1: 656 mg / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

6.1: tetrahydrofuran; acetonitrile; H₂O / 0.25 h / 20 °C

6.2: 72 percent / NaCNBH₃; aq. acetic acid / tetrahydrofuran; acetonitrile / 0.75 h / 20 °C

7.1: H₂ / PdCl₂ / ethanol / 12 h / 760 Torr

8.1: 352 mg / aq. NaHCO₃ / CH₂Cl₂ / 12 h / 20 °C

9.1: oxalyl chloride; DMF / CH₂Cl₂ / 0.33 h / 20 °C

10.1: 109 mg / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 °C

11.1: aq. HCO₂H / tetrahydrofuran / 0.75 h / 20 °C

12.1: 79 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; formic acid; oxalyl dichloride; hydrogen; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; trifluoroacetic acid; Pd-BaSO₄; palladium dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 12.1: Swern oxidation;

DOI:10.1021/ja0535918

Reference yield:

1-Benzyloxy-5-iodomethyl-2,4-dimethoxy-3-methyl-benzene (866110-56-7) → {2-(8-allyloxy-1-allyloxymethyl-3-formyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester (866110-69-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: 4.73 g / tetrahydrofuran / 4 h / -78 °C

2.1: H₂ / Pd/BaSO₄ / tetrahydrofuran / 24 h / 760 Torr

3.1: trifluoroacetic acid / CH₂Cl₂ / 12 h / 20 °C

4.1: 656 mg / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

5.1: tetrahydrofuran; acetonitrile; H₂O / 0.25 h / 20 °C

5.2: 72 percent / NaCNBH₃; aq. acetic acid / tetrahydrofuran; acetonitrile / 0.75 h / 20 °C

6.1: H₂ / PdCl₂ / ethanol / 12 h / 760 Torr

7.1: 352 mg / aq. NaHCO₃ / CH₂Cl₂ / 12 h / 20 °C

8.1: oxalyl chloride; DMF / CH₂Cl₂ / 0.33 h / 20 °C

9.1: 109 mg / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 °C

10.1: aq. HCO₂H / tetrahydrofuran / 0.75 h / 20 °C

11.1: 79 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; formic acid; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; Pd-BaSO₄; palladium dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 11.1: Swern oxidation;

DOI:10.1021/ja0535918

upstream raw materials:

{2-(8-allyloxy-1-allyloxymethyl-3-hydroxymethyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

1-Benzyloxy-5-iodomethyl-2,4-dimethoxy-3-methyl-benzene

(1R,3S)-8-Allyloxy-1-allyloxymethyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline

3-(tert-butyl-dimethyl-silanyloxymethyl)-8-hydroxy-1-hydroxymethyl-5,7-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Downstream raw materials:

C₃₃H₄₂N₂O₈

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