BOC-D-4-IODOPHENYLALANINE

Base Information

• Chemical Name: BOC-D-4-IODOPHENYLALANINE
• CAS No.: 176199-35-2
• Molecular Formula: C14H18INO4
• Molecular Weight: 391.206
• Hs Code.: 2924299090
• Mol file: 176199-35-2.mol

Synonyms:N-(tert-butoxycarbonyl)-4-iodo-D-phenylalanine;(2R)-3-(4-Iodophenyl)-2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)propanoic acid;4-Iodo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine;D-phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-iodophenyl)propanoic acid;4-Iodo-D-phenylalanine, N-BOC protected;Boc-4-iodo-D-phenylalanine;Boc-D-Phe(4-I)-OH;

Chemical Property of BOC-D-4-IODOPHENYLALANINE

Chemical Property:

• Vapor Pressure: 7.68E-10mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 475.3 °C at 760 mmHg
• Flash Point: 241.3 °C
• PSA: 75.63000
• Density: 1.56 g/cm³
• LogP: 3.20250
• Storage Temp.: Store at 0°C
• Sensitive.: Light Sensitive

Purity/Quality:

98%min ^*data from raw suppliers

Boc-D-4-Iodophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-D-4-IODOPHENYLALANINE

There total 2 articles about BOC-D-4-IODOPHENYLALANINE 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: 65.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-3-(4-iodophenyl)propanoic acid (62561-75-5) → (R)-2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoic acid (176199-35-2)

Guidance literature:

With triethylamine; In methanol; water; at 55 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jacs.8b07709

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (R)-2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoic acid (176199-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodate; iodine; acetic acid; sulfuric acid / 24 h / 70 °C / Inert atmosphere

1.2: 24 h / 70 °C / Inert atmosphere

1.3: 0 °C / pH 7

2.1: triethylamine / water; methanol / 16 h / 55 °C / Inert atmosphere

With sodium iodate; sulfuric acid; iodine; acetic acid; triethylamine; In methanol; water;

DOI:10.1021/jacs.8b07709

Reference yield: 92.0%

t-butyl bromide (507-19-7) + (R)-2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoic acid (176199-35-2) → Boc-D-Phe(4-I)-O-tBu

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl acetamide; at 0 - 55 ℃; for 2.5h;

DOI:10.1021/ol503630z

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-amino-3-(4-iodophenyl)propanoic acid

D-(R)-phenylalanine

Downstream raw materials:

(R)-2-tert-Butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid benzyl ester

tert-butyl [(2R)-1-hydroxy-3-(4-iodophenyl)propan-2-yl]carbamate

(R)-N-tert-butoxycarbonyl-4-(ethoxycarbonyl)phenylalaninol

(Z)-N-{(1R)-2-hydroxy-1-[[4-(ethoxycarbonyl)phenyl]methyl]ethyl}-9-octadecenamide

Refernces

• 1、 Ritzen, Andreas,Basu, Basudeb,Chattopadhyay, Shital K.,Dossa, Fahreen,Frejd, Torbjoern. "Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups". . p. 503 - 512. Retrieved 2007/10/03.