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

Base Information

• Chemical Name: [2-(5-allyloxy-1-benzyloxymethyl-7,8-dimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-benzyloxy-2-formyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester
• CAS No.: 851121-89-6
• Molecular Formula: C₄₈H₅₆N₂O₁₁
• Molecular Weight: 836.979
• Mol file: 851121-89-6.mol

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

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

There total 25 articles about [2-(5-allyloxy-1-benzyloxymethyl-7,8-dimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-benzyloxy-2-formyl-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: 84.0%

[2-(5-allyloxy-1-benzyloxymethyl-4-hydroxy-7,8-dimethoxy-6-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-benzyloxy-2-hydroxymethyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (851122-04-8) → [2-(5-allyloxy-1-benzyloxymethyl-7,8-dimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-benzyloxy-2-formyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (851121-89-6)

Guidance literature:

With 2,6-dimethylpyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ja050203t

Reference yield:

2-hydroxymethyl-3-iodo-6-methoxy-5-methyl-phenol (351379-10-7) → [2-(5-allyloxy-1-benzyloxymethyl-7,8-dimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-benzyloxy-2-formyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (851121-89-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 85 percent / K₂CO₃ / acetone / 4 h / Heating

2.1: sodium hydride / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

2.2: 99 percent / TBAI / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

3.1: 87 percent / TEA; TBABr; (o-tolyl)3P / Pd(OAc)2 / acetonitrile / 12 h / 80 °C

4.1: 93 percent / H₂; Rh[(COD)-(S,S)-Et-DuPhos]⁽¹⁺⁾*TfO^(1-) / CH₂Cl₂; methanol / 72 h / 20 °C / 5171.48 Torr

5.1: 93 percent / aq. LiOH / methanol; tetrahydrofuran / 11 h / 20 °C

6.1: 82 percent / sodium hydride / tetrahydrofuran / 15 h / 20 °C

7.1: BOPCl; TEA / CH₂Cl₂ / 72 h / 20 °C

8.1: DDQ; aq. buffer / CH₂Cl₂ / 0.5 h / 20 °C / pH 7.00

9.1: 84 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; (+)-1,2-bis((2S,,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; TEA; tetrabutylammomium bromide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; potassium carbonate; Dess-Martin periodane; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 3.1: Jeffery-Heck coupling;

DOI:10.1021/ja050203t

Reference yield:

toluene-4-sulfonic acid 5-iodo-2-methoxy-3-methyl-phenyl ester (351380-16-0) → [2-(5-allyloxy-1-benzyloxymethyl-7,8-dimethoxy-6-methyl-4-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-benzyloxy-2-formyl-4-methoxy-5-methyl-benzyl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester (851121-89-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 90 percent / aq. NaOH / ethane-1,2-diol / 5 h / Heating

2.1: Et₂AlCl / CH₂Cl₂ / 1 h / 20 °C

2.2: 86 percent / CH₂Cl₂ / 24 h / 20 °C

3.1: 85 percent / K₂CO₃ / acetone / 4 h / Heating

4.1: sodium hydride / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

4.2: 99 percent / TBAI / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

5.1: 87 percent / TEA; TBABr; (o-tolyl)3P / Pd(OAc)2 / acetonitrile / 12 h / 80 °C

6.1: 93 percent / H₂; Rh[(COD)-(S,S)-Et-DuPhos]⁽¹⁺⁾*TfO^(1-) / CH₂Cl₂; methanol / 72 h / 20 °C / 5171.48 Torr

7.1: 93 percent / aq. LiOH / methanol; tetrahydrofuran / 11 h / 20 °C

8.1: 82 percent / sodium hydride / tetrahydrofuran / 15 h / 20 °C

9.1: BOPCl; TEA / CH₂Cl₂ / 72 h / 20 °C

10.1: DDQ; aq. buffer / CH₂Cl₂ / 0.5 h / 20 °C / pH 7.00

11.1: 84 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium hydroxide; (+)-1,2-bis((2S,,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; TEA; tetrabutylammomium bromide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; diethylaluminium chloride; sodium hydride; potassium carbonate; Dess-Martin periodane; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; acetone; acetonitrile; 5.1: Jeffery-Heck coupling;

DOI:10.1021/ja050203t

upstream raw materials:

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

2-hydroxymethyl-3-iodo-6-methoxy-5-methyl-phenol

toluene-4-sulfonic acid 5-iodo-2-methoxy-3-methyl-phenyl ester

(2-benzyloxy-6-iodo-3-methoxy-4-methyl-phenyl)-methanol

Downstream raw materials:

C₄₆H₅₆N₂O₇Si

C₃₉H₄₈N₂O₉Si

C₃₉H₄₆N₂O₉Si

C₃₉H₄₈N₂O₈Si