Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid

Base Information

• Chemical Name: Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid
• CAS No.: 154672-64-7
• Molecular Formula: C₃₂H₃₈N₂O₆Si
• Molecular Weight: 574.749
• Mol file: 154672-64-7.mol

Synonyms:Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid

Chemical Property of Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid

There total 4 articles about Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid 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: 95.0%

(4S)-5-benzyloxy-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid (122350-52-1) + O-(2-trimethylsilylethyl)-hydroxylamine hydrochloride → Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid (154672-64-7)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1021/jo00083a041

Reference yield:

Fmoc-Glu(OtBu)-OH (71989-18-9) → Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid (154672-64-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 4-(dimethylamino)pyridine, DCC / CH₂Cl₂ / Ambient temperature

2: 91 percent / TFA / CH₂Cl₂ / 3.5 h

3: 95 percent / Et₃N, 1-hydroxy-1H-benzotriazole monohydrate, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂

With dmap; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00083a041

Reference yield:

Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-tert-butyl ester of L-glutamic acid (154672-63-6) → Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-N<2-(trimethylsilyl)ethoxy>amide of L-glutamic acid (154672-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / TFA / CH₂Cl₂ / 3.5 h

2: 95 percent / Et₃N, 1-hydroxy-1H-benzotriazole monohydrate, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00083a041

upstream raw materials:

(4S)-5-benzyloxy-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid

Fmoc-Glu(OtBu)-OH

Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-tert-butyl ester of L-glutamic acid

benzyl alcohol

Downstream raw materials:

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxyamino)-pentanoic acid benzyl ester