(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:175550-96-6
Molecular Formula:C₃₁H₅₅NO₃Si
Molecular Weight:517.868
Hs Code.:

Synonyms:(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

There total 38 articles about (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-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: 100.0%

: C₃₁H₅₃NO₃Si

: 175550-96-6
(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; under 760.051 Torr;
DOI:10.1515/hc-2013-0236

Reference yield: 62.0%

: 892859-71-1
(-)-((1R,3S)-3-(tert-butyldimethylsilyloxy)-1-nonylpent-4-enyl)-carbamic acid tert-butyl ester

: 108-86-1,52753-63-6
bromobenzene

: 175550-96-6
(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium t-butanolate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In toluene; at 90 ℃;
DOI:10.1021/ol0606435

Reference yield:

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

: 175550-96-6
(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1.10 g / NaOH / H₂O; dioxane; tetrahydrofuran / 14 h / 20 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 67 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

3.1: CuBr₂*Me₂S / diethyl ether / -20 °C

3.2: 56 percent / diethyl ether / 2 h / -78 °C

4.1: 93 percent / imidazole / dimethylformamide / 20 °C

5.1: 62 percent / NaOtBu / Pd(OAc)2; bis(2-diphenylphosphinophenyl) ether / toluene / 90 °C

With 1H-imidazole; sodium hydroxide; copper bromide dimethyl sulfide complex; ozone; sodium t-butanolate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol0606435