BOC-P-IODO-DL-PHE-OH

Base Information

• Chemical Name: BOC-P-IODO-DL-PHE-OH
• CAS No.: 103882-09-3
• Molecular Formula: C14H18 I N O4
• Molecular Weight: 391.206
• Mol file: 103882-09-3.mol

Synonyms:BOC-4-IODO-DL-PHENYLALANINE;BOC-DL-PHE(4-I)-OH;BOC-DL-PHE(P-I)-OH;BOC-P-IODO-DL-PHENYLALANINE;BOC-P-IODO-DL-PHE-OH;N-T-BUTOXYCARBONYL-P-IODO-DL-PHENYLALANINE

Chemical Property of BOC-P-IODO-DL-PHE-OH

Chemical Property:

• PSA: 75.63000
• LogP: 3.20250

Purity/Quality:

99.3% ^*data from raw suppliers

Boc-4-iodo-DL-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-P-IODO-DL-PHE-OH

There total 10 articles about BOC-P-IODO-DL-PHE-OH 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-iodo-L-phenylalanine (1991-81-7,14173-41-2,24250-85-9,62561-75-5) → N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6)

Guidance literature:

4-iodo-L-phenylalanine; With sodium hydroxide; In 1,4-dioxane; water; at 19 ℃;

di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 0 - 30 ℃; for 8h;

Reference yield:

4-iodo-L-phenylalanine (1991-81-7,14173-41-2,24250-85-9,62561-75-5) + N-ethyl-N,N-diisopropylamine (7087-68-5) → N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6)

Guidance literature:

With hydrogenchloride; sodium hydroxide; sulfuric acid; In dichloromethane; diethylene glycol dimethyl ether; ethyl acetate;

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodate; sulfuric acid; iodine / acetic acid / 18 h / 70 °C

1.2: 0.5 h / 70 °C

2.1: sodium hydroxide / tert-butyl alcohol / 18 h / 20 °C

With sodium iodate; sulfuric acid; iodine; sodium hydroxide; In acetic acid; tert-butyl alcohol;

DOI:10.1021/ja209352s

upstream raw materials:

di-tert-butyl dicarbonate

4-iodo-L-phenylalanine

1-bromomethyl-4-iodobenzene

diethyl tert-butoxycarbonylaminomalonate

Downstream raw materials:

N-Boc-4-formyl-L-phenylalanine

N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester

benzyl Boc-4-iodophenylalanine

2-tert-butoxycarbonylamino-3-{4-[3-(2,2,2-trifluoro-acetylamino)-prop-1-ynyl]-phenyl}-propionic acid

Refernces

• 1、 Malan, Christophe,Morin, Christophe. "A concise preparation of 4-borono-l-phenylalanine (L-BPA) from L-phenylalanine". . p. 8019 - 8020. Retrieved 1998.
• 2、 Cuesta-Galisteo, Sergio,Sch?rgenhumer, Johannes,Wei, Xiaofeng,Merino, Estíbaliz,Nevado, Cristina. "Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides". supporting information. p. 1605 - 1609. Retrieved 2020/12/01.
• 3、 Rajput, Sunnia,McLean, Kirsty J.,Poddar, Harshwardhan,Selvam, Irwin R.,Nagalingam, Gayathri,Triccas, James A.,Levy, Colin W.,Munro, Andrew W.,Hutton, Craig A.. "Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct". supporting information. p. 9792 - 9805. Retrieved 2019/11/13.