Boc-D-isoleucine

Base Information

• Chemical Name: Boc-D-isoleucine
• CAS No.: 55721-65-8
• Molecular Formula: C11H21NO4
• Molecular Weight: 231.292
• Hs Code.: 29224999
• Mol file: 55721-65-8.mol

Synonyms:N-tert-Butoxycarbonyl-D-isoleucine;

Chemical Property of Boc-D-isoleucine

Chemical Property:

• Melting Point: 63-65 °C
• Refractive Index: 1.461
• Boiling Point: 356.041 °C at 760 mmHg
• PKA: 4.03±0.22(Predicted)
• Flash Point: 169.128 °C
• PSA: 75.63000
• Density: 1.062 g/cm³
• LogP: 2.40130
• Storage Temp.: −20°C

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-Ile-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-D-isoleucine is an N-Boc-protected form of D-Isoleucine (I820210). D-Isoleucine is not biosynthesized in the human body and is therefore categorized as an essential amino acid that must be obtained through diet. It is also an important building block that is used in the formation of hemoglobin in humans.

Technology Process of Boc-D-isoleucine

There total 37 articles about Boc-D-isoleucine 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: 99.0%

D-allo-isoleucine (1509-34-8,959215-79-3,18875-42-8) + di-tert-butyl dicarbonate (24424-99-5) → Boc-L-aIle-OH (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 2h; 0 deg C to r. t.;

DOI:10.1021/jo00037a012

Reference yield: 96.0%

D-alloisoleucine (1509-35-9,959215-79-3,18875-42-8) + 2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile → N-tert-butoxycarbonyl-D-alloisoleucine (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9)

Guidance literature:

With triethylamine; In water; acetone; for 5h; Ambient temperature;

DOI:10.1021/jo00037a012

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2RS,3S)-2-amino-3-methylpentanoic acid (959215-79-3,18875-42-8) → N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + N-tert-butoxycarbonyl-D-alloisoleucine (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 22 ℃; pH=9 - 10; Overall yield = 88 %; Overall yield = 0.77 g; diastereoselective reaction;

DOI:10.1039/c5ob02520f

upstream raw materials:

L-isoleucine

1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

tert-butyl alcohol

di-tert-butyl dicarbonate

Downstream raw materials:

Boc-Ileu-(N^ε-Z-Lys-OCH3)

tert-(butoxycarbonyl)isoleucine succinimidyl ester

Boc-L-aIle-L-MeVal-OPac

tert-butyl (1S,2R)-1-(hydroxymethyl)-2-methylbutylcarbamate

Refernces

• 1、 Srinivasarao, Kondaparla,Agarwal, Pooja,Srivastava, Kumkum,Haq,Puri, Sunil K.,Katti. "Design, synthesis, and in vitro antiplasmodial activity of 4-aminoquinolines containing modified amino acid conjugates". . p. 1148 - 1162. Retrieved 2016/07/06.
• 2、 Mevers, Emily,Haeckl, F. P. Jake,Boudreau, Paul D.,Byrum, Tara,Dorrestein, Pieter C.,Valeriote, Frederick A.,Gerwick, William H.. "Lipopeptides from the tropical marine cyanobacterium symploca sp.". . p. 969 - 975. Retrieved 2014/05/20.