(2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

Base Information

Chemical Name:(2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate
CAS No.:189098-09-7
Molecular Formula:C₁₉H₂₅NO₅
Molecular Weight:347.411
Hs Code.:

Synonyms:(2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

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Chemical Property of (2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

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Technology Process of (2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

There total 4 articles about (2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate 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: 71.0%

: 100-52-7
benzaldehyde

: 189098-08-6
(S)-ethyl 4,4-dimethyl-N-propionylpyroglutamate

: 189098-09-7
(2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ol034847m

Reference yield:

: 221637-35-0
(S)-ethyl 4,4-dimethyl-5-oxopyrrolidine-2-carboxylate

: 189098-09-7
(2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / n-BuLi

2: 71 percent / Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ol034847m

Reference yield:

: 144978-35-8,144978-12-1,251924-83-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate

: 189098-09-7
(2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LiHMDS / 2.) THF, from -78 deg C to RT

2: TFA / CH₂Cl₂ / Ambient temperature

3: 80 percent / BuLi / -78 °C

4: 1.) Bu₂BOTf, iPr₂NEt / 1.) CH₂Cl₂, THF, 0 deg C, 2.) CH₂Cl₂

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1016/S0957-4166(97)00028-1