2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester
CAS No.:410072-05-8
Molecular Formula:C₅₆H₈₇NO₉Si₃
Molecular Weight:1002.56
Hs Code.:

2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

Synonyms:2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

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Chemical Property of 2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

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Technology Process of 2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

There total 12 articles about 2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-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: 86.7%

: 24424-99-5
di-tert-butyl dicarbonate

: 410071-93-1
(4R,6S)-4-(tert-butyldiphenylsilyloxymethyl)-2-{3-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indol-2-yl}-6-(triethylsilyloxymethyl)-6-(trimethylsilyloxy)octanoic acid methyl ester

: 410072-05-8
2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 14h;
DOI:10.1021/ja0177049

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 410072-05-8
2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 91.5 percent / imidazole / dimethylformamide / 1 h / 20 °C

2.1: DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

3.1: H₂NOH*HCl; NaOAc / ethanol / 1 h / 20 °C

4.1: 20.0 g / aq. NaClO / CH₂Cl₂ / 3.5 h / 20 °C

5.1: 66.4 percent / Zn; AcOH / 4 h / 20 °C

6.1: mCPBA; AcOH / 41 h / 20 °C

7.1: 9.49 g / K₂CO₃ / 0.75 h / 20 °C

8.1: imidazole / dimethylformamide / 1 h / 20 °C

9.1: 7.125 g / dimethylformamide / 0.67 h / 20 °C

10.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1.17 h / -78 °C

10.2: 75.73 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

11.1: 67.39 percent / Bu₃SnH; Et₃B / tetrahydrofuran / 1 h / 20 °C

12.1: 86.7 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

With 1H-imidazole; dmap; sodium hypochlorite; n-butyllithium; triethyl borane; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium acetate; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja0177049

Reference yield:

: 4-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethyl-hept-6-enal

: 410072-05-8
2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-1-(methoxycarbonyl)-5-(triethylsilyloxymethyl)-5-(trimethylsilyloxy)heptyl]-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: H₂NOH*HCl; NaOAc / ethanol / 1 h / 20 °C

2.1: 20.0 g / aq. NaClO / CH₂Cl₂ / 3.5 h / 20 °C

3.1: 66.4 percent / Zn; AcOH / 4 h / 20 °C

4.1: mCPBA; AcOH / 41 h / 20 °C

5.1: 9.49 g / K₂CO₃ / 0.75 h / 20 °C

6.1: imidazole / dimethylformamide / 1 h / 20 °C

7.1: 7.125 g / dimethylformamide / 0.67 h / 20 °C

8.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1.17 h / -78 °C

8.2: 75.73 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

9.1: 67.39 percent / Bu₃SnH; Et₃B / tetrahydrofuran / 1 h / 20 °C

10.1: 86.7 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

With 1H-imidazole; dmap; sodium hypochlorite; n-butyllithium; triethyl borane; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium acetate; potassium carbonate; acetic acid; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja0177049