(2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Base Information

Chemical Name:(2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
CAS No.:795306-42-2
Molecular Formula:C₂₅H₄₂BrNO₃Si
Molecular Weight:512.603
Hs Code.:

Synonyms:(2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

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Chemical Property of (2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

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Technology Process of (2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

There total 5 articles about (2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 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: 92.0%

: 795306-40-0
[(S)-2-Bromo-1-((R)-2-iodo-1-methyl-ethyl)-allyloxy]-tert-butyl-dimethyl-silane

: 159213-03-3
N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

: 795306-42-2
(2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:: N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.33333h;

[(S)-2-Bromo-1-((R)-2-iodo-1-methyl-ethyl)-allyloxy]-tert-butyl-dimethyl-silane; In tetrahydrofuran; hexane; at 0 ℃; for 18h;
DOI:10.1039/b410092a

Reference yield:

: 795306-24-0
(2S,3S)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-4-en-1-ol

: 795306-42-2
(2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / Ph₃P; imidazole; iodine / CH₂Cl₂ / 12 h / 20 °C

2.1: LDA; LiCl / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

2.2: 92 percent / tetrahydrofuran; hexane / 18 h / 0 °C

With 1H-imidazole; iodine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 2.2: Myers alkylation;
DOI:10.1039/b410092a

Reference yield:

: 795306-38-6
(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

: 795306-42-2
(2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 62 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: 86 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

3.1: 88 percent / Ph₃P; imidazole; iodine / CH₂Cl₂ / 12 h / 20 °C

4.1: LDA; LiCl / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

4.2: 92 percent / tetrahydrofuran; hexane / 18 h / 0 °C

With 1H-imidazole; iodine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 4.2: Myers alkylation;
DOI:10.1039/b410092a