DL-Phenylalanine, 4-borono-

Base Information

• Chemical Name: DL-Phenylalanine, 4-borono-
• CAS No.: 77374-29-9
• Molecular Formula: C₉H₁₂BNO₄
• Molecular Weight: 209.01
• Mol file: 77374-29-9.mol

Synonyms:

Chemical Property of DL-Phenylalanine, 4-borono-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-Phenylalanine, 4-borono-

There total 4 articles about DL-Phenylalanine, 4-borono- 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: 83.0%

Methyl 2-amino-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]propionate → DL-4-boronophenylalanine (76410-58-7,77374-29-9,90580-64-6,111821-49-9)

Guidance literature:

Methyl 2-amino-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]propionate; With sodium hydroxide; water; at 45 - 50 ℃; for 2h;

With hydrogenchloride; water; at 30 ℃; for 3h;

DOI:10.1055/s-1999-3624

Reference yield:

N-acetyl-4-dihydroxyboranyl-phenylalanine (147529-10-0) → DL-4-boronophenylalanine (76410-58-7,77374-29-9,90580-64-6,111821-49-9)

Guidance literature:

N-acetyl-4-dihydroxyboranyl-phenylalanine; With hydrogenchloride; In water; at 85 - 100 ℃; for 12 - 18h;

With sodium hydroxide; In water; at 18 - 25 ℃; pH=6;

Reference yield:

Methyl (E/Z)-2-(benzyloxycarbonylamino)-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acrylate → DL-4-boronophenylalanine (76410-58-7,77374-29-9,90580-64-6,111821-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / H₂ / 10 percent Pd/C / methanol; CH₂Cl₂ / 19 h / 20 °C / 2280 Torr

2.1: NaOH; H₂O / 2 h / 45 - 50 °C

2.2: 83 percent / HCl; H₂O / 3 h / 30 °C

With sodium hydroxide; water; hydrogen; 10% palladium on active carbon; In methanol; dichloromethane; 1.1: Hydrogenation / 2.1: Hydrolysis / 2.2: Hydrolysis;

DOI:10.1055/s-1999-3624

upstream raw materials:

N-acetyl-4-dihydroxyboranyl-phenylalanine

Downstream raw materials:

3-[4-(thien-3-yl)phenyl]alanine

2-amino-3-(2'-fluoro-biphenyl-4-yl)-propionic acid

C₁₅H₂₂BNO₆

t-butyl(phenyl)nitroxide

Refernces

• 1、 Park, Ki Chul,Yoshino, Kazuo,Tomiyasu, Hiroshi. "A high-yield synthesis of 4-borono-DL-phenylalanine". . p. 2041 - 2044. Retrieved 2007/10/03.