Cbz-L-propargylglycine-L-Phe-NH₂

Base Information

• Chemical Name: Cbz-L-propargylglycine-L-Phe-NH₂
• CAS No.: 917599-66-7
• Molecular Formula: C₂₂H₂₃N₃O₄
• Molecular Weight: 393.442
• Mol file: 917599-66-7.mol

Synonyms:Cbz-L-propargylglycine-L-Phe-NH₂

Chemical Property of Cbz-L-propargylglycine-L-Phe-NH₂

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cbz-L-propargylglycine-L-Phe-NH₂

There total 4 articles about Cbz-L-propargylglycine-L-Phe-NH₂ 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: 79.0%

Cbz-L-propargylglycine-OMe (917599-63-4) + L-Phenylalanine amide (5241-58-7) → Cbz-L-propargylglycine-L-Phe-NH2 (917599-66-7)

Guidance literature:

With Bacillus licheniformis alcalase; In N,N-dimethyl-formamide; tert-butyl alcohol; at 35 ℃;

DOI:10.1055/s-2006-942509

Reference yield:

Cbz-L-propargylglycine-OMe (917599-63-4) → Cbz-L-propargylglycine-L-Phe-NH2 (917599-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. KHCO₃ / 2-methyl-propan-2-ol / 0.08 h

2.1: DIPEA; EDCI; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 0.5 h / 0 - 5 °C

2.2: dimethylformamide / 20 °C

With 1-hydroxy-7-aza-benzotriazole; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-2006-942509

Reference yield:

(2S)-2-amino-4-pentynoic acid (23235-01-0) → Cbz-L-propargylglycine-L-Phe-NH2 (917599-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / 2 h / Heating

2: 162 mg / aq. NaOH; NaHCO₃ / dioxane / 18 h / 20 °C

3: 79 percent / Bacillus licheniformis alcalase / dimethylformamide; 2-methyl-propan-2-ol / 35 °C

With sodium hydroxide; thionyl chloride; sodium hydrogencarbonate; In 1,4-dioxane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-2006-942509

upstream raw materials:

Cbz-L-propargylglycine-OMe

L-Phenylalanine amide

(2S)-2-amino-4-pentynoic acid

(S)-propargylglycine methyl ester

Refernces

• 1、 Groothuys, Stan,Kuijpers, Brian H. M.,Quaedflieg, Peter J. L. M.,Roelen, Harlof C. P. F.,Wiertz, Roel W.,Blaauw, Richard H.,Van Delft, Floris L.,Rutjes, Floris P. J. T.. "Chemoenzymatic synthesis of triazole-linked glycopeptides". . p. 3146 - 3152. Retrieved 2008/02/09.