(2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Base Information

Chemical Name:(2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
CAS No.:365404-50-8
Molecular Formula:C₃₁H₄₉NO₄Si
Molecular Weight:527.82
Hs Code.:

Synonyms:(2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

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Chemical Property of (2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

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Technology Process of (2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

There total 4 articles about (2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-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:

: 64714-79-0
5-benzyloxy-3-oxo-pentanoic acid ethyl ester

: 365404-50-8
(2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1.1: H₂; benzeneruthenium (II) chloride dimer; (R)-(+)-BINAP / ethanol; dimethylformamide / 90 h / 20 - 40 °C / 62059.4 Torr

2.1: 86 percent / imidazole / dimethylformamide / 9 h / 20 °C

3.1: 88 percent / DIBALH / CH₂Cl₂; hexane / 0.33 h / -30 - -25 °C

4.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 17 h / 20 °C

5.1: diisopropylamine; LiCl; n-butyllithium / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

5.2: 98 percent / tetrahydrofuran; hexane / 20 h / 0 - 20 °C

With 1H-imidazole; dichloro(benzene)ruthenium(II) dimer; n-butyllithium; hydrogen; iodine; diisobutylaluminium hydride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Noyori hydrogenation;
DOI:10.1021/ja011377n

Reference yield:

: 113335-04-9
(R)-5-Benzyloxy-3-hydroxy-pentanoic acid ethyl ester

: 365404-50-8
(2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / imidazole / dimethylformamide / 9 h / 20 °C

2.1: 88 percent / DIBALH / CH₂Cl₂; hexane / 0.33 h / -30 - -25 °C

3.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 17 h / 20 °C

4.1: diisopropylamine; LiCl; n-butyllithium / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

4.2: 98 percent / tetrahydrofuran; hexane / 20 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; iodine; diisobutylaluminium hydride; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja011377n

Reference yield:

: 365404-49-5
(S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentan-1-ol

: 365404-50-8
(2S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 17 h / 20 °C

2.1: diisopropylamine; LiCl; n-butyllithium / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

2.2: 98 percent / tetrahydrofuran; hexane / 20 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; iodine; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja011377n