allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester
• CAS No.: 312731-79-6
• Molecular Formula: C₄₄H₆₅NO₈Si
• Molecular Weight: 764.087
• Mol file: 312731-79-6.mol

Synonyms:allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester

Chemical Property of allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester

There total 12 articles about allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-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: 85.0%

allyl bromide (106-95-6) + {3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester (312731-69-4) → allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester (312731-79-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/ja0013879

Reference yield:

isonitrovanillin (6635-20-7) → allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester (312731-79-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / HBr; AcOH / H₂O / 8 h / Heating

2: 85 percent / NaH / dimethylformamide

3: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4: 80 percent / dimethylformamide / 1 h

5: 96 percent / TsOH / methanol / 3 h / Heating

6: 49 percent / DIBAL-H / toluene / 0.83 h / 0 - 20 °C

7: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / 0.75 h

8: 82 percent / DIBAL-H / toluene / 0 - 10 °C

9: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

10: 79 percent / H₂ / Raney-Ni / methanol; tetrahydrofuran / 19 h

11: 64 percent / NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

12: 85 percent / NaH / dimethylformamide; tetrahydrofuran / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogen bromide; hydrogen; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0013879

Reference yield:

3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → allyl-{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester (312731-79-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / NaH / dimethylformamide

2: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3: 80 percent / dimethylformamide / 1 h

4: 96 percent / TsOH / methanol / 3 h / Heating

5: 49 percent / DIBAL-H / toluene / 0.83 h / 0 - 20 °C

6: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / 0.75 h

7: 82 percent / DIBAL-H / toluene / 0 - 10 °C

8: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

9: 79 percent / H₂ / Raney-Ni / methanol; tetrahydrofuran / 19 h

10: 64 percent / NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

11: 85 percent / NaH / dimethylformamide; tetrahydrofuran / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogen; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0013879

upstream raw materials:

allyl bromide

{3-benzyloxy-5-dimethoxymethyl-2-[2-(4-methoxy-benzyloxy)-1-triisopropylsilanyloxymethyl-ethyl]-phenyl}-carbamic acid tert-butyl ester

isonitrovanillin

3,4-dihydroxy-5-nitrobenzaldehyde