[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

Base Information

Chemical Name:[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide
CAS No.:669065-55-8
Molecular Formula:C₄₂H₇₆Cl₃NO₉Si₂
Molecular Weight:901.597
Hs Code.:

[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

Synonyms:[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

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Chemical Property of [1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

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Technology Process of [1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

There total 22 articles about [1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide 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: 91.0%

: 669065-54-7
[1(3Z,5R,6S,7S),3R]-N-{3-[7,9-bis(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-(tert-butyldimethylsilyloxy)-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

: 669065-55-8
[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 - 20 ℃; for 2h;
DOI:10.1021/ol036284k

Reference yield:

: 669065-40-1
(R)-4-(tert-butyldimethylsilyloxy)-3-methoxy-butyric acid benzyl ester

: 669065-55-8
[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / H₂ / Pd/C / methanol / 1.5 h

2.1: Et₃N; ClCO₂Et / CH₂Cl₂ / 0.67 h / -20 °C

2.2: 91 percent / NH₃ gas / CH₂Cl₂ / -10 °C

3.1: 82 percent / K₂CO₃; CuI; N,N'-dimethylethylenediamine / toluene / 36 h / 110 °C

4.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 73 percent / tetrahydrofuran / 8 h / -78 - -30 °C

5.1: 96 percent / Na₂HPO₄; Na/Hg / methanol / 1.5 h / -20 °C

6.1: KH / tetrahydrofuran / 0.15 h / 0 °C

6.2: 95 percent / tetrahydrofuran / 0.33 h / 20 °C

7.1: 91 percent / HF*pyr / pyridine; tetrahydrofuran / 2 h / 0 - 20 °C

With disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; hydrogen; chloroformic acid ethyl ester; potassium hydride; potassium carbonate; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; N,N`-dimethylethylenediamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene;
DOI:10.1021/ol036284k

Reference yield:

: 672-13-9
2-hydroxy-5-methoxybenzaldehyde

: 669065-55-8
[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 89 percent / AcONa; Br₂ / acetic acid / 1 h / 20 °C

2.1: 99 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

3.1: 100 percent / BH₃*THF / tetrahydrofuran / 1 h / 0 °C

4.1: 96 percent / PPh₄; CBr₄ / tetrahydrofuran / 1 h / 20 °C

5.1: 86 percent / dimethylformamide / 24 h / 20 °C

6.1: 82 percent / K₂CO₃; CuI; N,N'-dimethylethylenediamine / toluene / 36 h / 110 °C

7.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

7.2: 73 percent / tetrahydrofuran / 8 h / -78 - -30 °C

8.1: 96 percent / Na₂HPO₄; Na/Hg / methanol / 1.5 h / -20 °C

9.1: KH / tetrahydrofuran / 0.15 h / 0 °C

9.2: 95 percent / tetrahydrofuran / 0.33 h / 20 °C

10.1: 91 percent / HF*pyr / pyridine; tetrahydrofuran / 2 h / 0 - 20 °C

With disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; borane-THF; carbon tetrabromide; bromine; sodium acetate; tetraphenylphosphonium; potassium hydride; potassium carbonate; pyridine hydrogenfluoride; lithium hexamethyldisilazane; N,N`-dimethylethylenediamine; In tetrahydrofuran; pyridine; methanol; acetic acid; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol036284k