N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester

Base Information

• Chemical Name: N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester
• CAS No.: 357958-50-0
• Molecular Formula: C₂₂H₃₅NO₆Si
• Molecular Weight: 437.608

Synonyms:N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester

Chemical Property of N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester

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Technology Process of N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester

There total 5 articles about N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl 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: 86.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt (34897-61-5) → N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester (357958-50-0)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 36h;

DOI:10.1055/s-2002-35616

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester (357958-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC; DMAP / CH₂Cl₂

2: NaOH / tetrahydrofuran

3: H⁺

With dmap; sodium hydroxide; hydrogen cation; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0960-894X(01)00103-2

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester (357958-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC; DMAP / CH₂Cl₂

2: NaOH / tetrahydrofuran

3: H⁺

With dmap; sodium hydroxide; hydrogen cation; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0960-894X(01)00103-2

upstream raw materials:

isobutene

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-(2-trimethylsilanyl-ethyl) ester

2-(Trimethylsilyl)ethanol

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt

Downstream raw materials:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

(S)-2-((S)-4-Benzyloxycarbonylamino-2,2-difluoro-5-hydroxy-pentanoylamino)-pentanedioic acid 1-tert-butyl ester 5-(2-trimethylsilanyl-ethyl) ester

N-Cbz-difluorooxazolidine-γ-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester

N-Cbz-(2S)-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester

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