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

Base Information

Chemical Name:(4R,6S)-4-(tert-butyldiphenylsilyloxymethyl)-2-{3-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indol-2-yl}-6-(triethylsilyloxymethyl)-6-(trimethylsilyloxy)octanoic acid methyl ester
CAS No.:410071-93-1
Molecular Formula:C₅₁H₇₉NO₇Si₃
Molecular Weight:902.447
Hs Code.:

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

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

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

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

There total 11 articles about (4R,6S)-4-(tert-butyldiphenylsilyloxymethyl)-2-{3-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indol-2-yl}-6-(triethylsilyloxymethyl)-6-(trimethylsilyloxy)octanoic acid methyl 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: 67.39%

: 410071-92-0
(4R,6S)-4-(tert-butyldiphenylsilyloxymethyl)-2-{2-[(Z)-3-(tetraydropyran-2-yloxy)propenyl]phenylthiocarbamoyl}-6-(triethylsilyloxymethyl)-6-(trimethylsilyloxy)octanoic acid methyl ester

: 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

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ja0177049

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 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

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; sodium hypochlorite; n-butyllithium; triethyl borane; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium acetate; diisobutylaluminium hydride; potassium carbonate; acetic acid; 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

: 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

Guidance literature:: Multi-step reaction with 9 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

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