6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester
• CAS No.: 186355-49-7
• Molecular Formula: C₂₈H₃₉N₃O₄Si
• Molecular Weight: 509.721
• Mol file: 186355-49-7.mol

Synonyms:6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Chemical Property of 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

There total 1 articles about 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic 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%

di-tert-butyl dicarbonate (24424-99-5) + (S)-6-Amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile (174873-28-0) → 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (186355-49-7)

Guidance literature:

In acetonitrile; at 90 ℃; for 16h;

DOI:10.1021/ja962431g

Reference yield: 97.0%

formic acid (64-18-6) + 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (186355-49-7) → 7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-6-formylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (186355-50-0)

Guidance literature:

With acetic anhydride; at 25 ℃; for 1h;

DOI:10.1021/ja962431g

Reference yield:

6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (186355-49-7) → methyl (2R,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate (174873-35-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / Ac₂O / 1 h / 25 °C

2.1: 78 percent / NaH / dimethylformamide / 7 h / 0 °C

3.1: TsOH; H₂O / tetrahydrofuran / 2 h / 0 °C

4.1: HCl / methanol / 5 h / 25 °C

4.2: 3.3 mg / EDCI / dimethylformamide / 48 h / 25 °C

With hydrogenchloride; water; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Formylation / 2.1: Alkylation / 2.2: Dieckmann cyclization / 3.1: Hydrolysis / 4.1: deprotection / 4.2: Acylation;

DOI:10.1021/ja962431g

upstream raw materials:

di-tert-butyl dicarbonate

(S)-6-Amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

Downstream raw materials:

7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-cyano-6-formylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

duocarmycin A

methyl (2R,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

methyl (2R,8S)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate