O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate

Base Information

• Chemical Name: O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate
• CAS No.: 312327-06-3
• Molecular Formula: C₃₄H₄₂N₂O₆Si
• Molecular Weight: 602.803
• Mol file: 312327-06-3.mol

Synonyms:O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate

Chemical Property of O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate

There total 10 articles about O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate 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: 96.0%

O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-4(1H)-quinolinon-5-yl]ethyl carbamate (312327-30-3) + methyl iodide (74-88-4) → O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate (312327-06-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

DOI:10.1021/jo001080s

Reference yield:

isonitrovanillin (6635-20-7) → O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate (312327-06-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / AlCl₃; pyridine / CHCl₃ / 24 h / Heating

2: 93 percent / dimethylformamide / 48 h / 140 °C

3: 92 percent / KOH; benzyltriethylammonium chloride / CHCl₃ / 36 h / 20 °C

4: Amberlyst A-21 ion-exchange resin / tetrahydrofuran / 3 h / 20 °C

5: 1.86 g / 2,6-lutidine / tetrahydrofuran / 2 h / 0 - 20 °C

6: 76 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran / 25 h / 0 °C

7: 97 percent / DMAP; K₂CO₃ / tetrahydrofuran / -78 - -30 °C

8: 90 percent / trimethyl orthoformate / 12 h / Heating

9: 82 percent / diphenyl ether / 0.33 h / 240 °C

10: 96 percent / K₂CO₃ / dimethylformamide / 3 h / 100 °C

With pyridine; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; aluminium trichloride; Amberlyst A-21 ion-exchange resin; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; nickel dichloride; trimethyl orthoformate; In tetrahydrofuran; methanol; diphenylether; chloroform; N,N-dimethyl-formamide; 1: ether cleavage / 2: Alkylation / 3: Methylation / 4: Addition / 5: silylation / 6: Reduction / 7: benzyloxycarbonylation / 8: Condensation / 9: Cyclization / 10: Methylation;

DOI:10.1021/jo001080s

Reference yield:

3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-1-methyl-4(1H)-quinolinon-5-yl]ethyl carbamate (312327-06-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / dimethylformamide / 48 h / 140 °C

2: 92 percent / KOH; benzyltriethylammonium chloride / CHCl₃ / 36 h / 20 °C

3: Amberlyst A-21 ion-exchange resin / tetrahydrofuran / 3 h / 20 °C

4: 1.86 g / 2,6-lutidine / tetrahydrofuran / 2 h / 0 - 20 °C

5: 76 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran / 25 h / 0 °C

6: 97 percent / DMAP; K₂CO₃ / tetrahydrofuran / -78 - -30 °C

7: 90 percent / trimethyl orthoformate / 12 h / Heating

8: 82 percent / diphenyl ether / 0.33 h / 240 °C

9: 96 percent / K₂CO₃ / dimethylformamide / 3 h / 100 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; Amberlyst A-21 ion-exchange resin; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; nickel dichloride; trimethyl orthoformate; In tetrahydrofuran; methanol; diphenylether; chloroform; N,N-dimethyl-formamide; 1: Alkylation / 2: Methylation / 3: Addition / 4: silylation / 5: Reduction / 6: benzyloxycarbonylation / 7: Condensation / 8: Cyclization / 9: Methylation;

DOI:10.1021/jo001080s

upstream raw materials:

O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[7-benzyloxy-8-methoxy-4(1H)-quinolinon-5-yl]ethyl carbamate

methyl iodide

isonitrovanillin

3,4-dihydroxy-5-nitrobenzaldehyde