N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester

Base Information

• Chemical Name: N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester
• CAS No.: 323196-10-7
• Molecular Formula: C₃₇H₃₈N₂O₃
• Molecular Weight: 558.72
• Mol file: 323196-10-7.mol

Synonyms:N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester

Chemical Property of N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester

There total 8 articles about N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl 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: 27.0%

DL-valine methyl ester hydrochloride (5619-05-6,6306-52-1,7146-15-8) + 2-cyanoethyl N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoic acid (323196-08-3) → N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(R)-valine methyl ester + N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester (323196-10-7)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1016/S0040-4020(00)00826-7

Reference yield:

L-allylglycine (16338-48-0) → N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester (323196-10-7)

Guidance literature:

Multi-step reaction with 7 steps

1: NaHCO₃ / dioxane / 24 h / 20 °C

2: 67 percent / 4,4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 20 h

3: 84 percent / HCl / dioxane / 2 h / 20 °C

4: 73 percent / NaBH₃CN / methanol / 19 h / 20 °C

5: 83 percent / K₃PO₄; Pb(NO₃)2 / acetonitrile / 17 h / 20 °C

6: 92 percent / K₂CO₃*1.5H₂O / tetrahydrofuran; methanol; H₂O / 14 h / 20 °C

7: 27 percent / pyridine; DCC / CH₂Cl₂ / 18 h / 20 °C

With pyridine; hydrogenchloride; dmap; potassium phosphate; lead(II) nitrate; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 1: Acylation / 2: Esterification / 3: Elimination / 4: reductive alkylation / 5: Substitution / 6: Hydrolysis / 7: Acylation;

DOI:10.1016/S0040-4020(00)00826-7

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) → N-(N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoyl)-(S)-valine methyl ester (323196-10-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 67 percent / 4,4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 20 h

2: 84 percent / HCl / dioxane / 2 h / 20 °C

3: 73 percent / NaBH₃CN / methanol / 19 h / 20 °C

4: 83 percent / K₃PO₄; Pb(NO₃)2 / acetonitrile / 17 h / 20 °C

5: 92 percent / K₂CO₃*1.5H₂O / tetrahydrofuran; methanol; H₂O / 14 h / 20 °C

6: 27 percent / pyridine; DCC / CH₂Cl₂ / 18 h / 20 °C

With pyridine; hydrogenchloride; dmap; potassium phosphate; lead(II) nitrate; sodium cyanoborohydride; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 1: Esterification / 2: Elimination / 3: reductive alkylation / 4: Substitution / 5: Hydrolysis / 6: Acylation;

DOI:10.1016/S0040-4020(00)00826-7

upstream raw materials:

DL-valine methyl ester hydrochloride

2-cyanoethyl N-benzyl-N-phenylfluorenyl-(S)-2-amino-4-pentenoic acid

L-allylglycine

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid