N-[(benzyloxy)carbonyl]alanylthreonine

Base Information

• Chemical Name: N-[(benzyloxy)carbonyl]alanylthreonine
• CAS No.: 78609-60-6
• Molecular Formula: C15H20N2O6
• Molecular Weight: 324.334
• Mol file: 78609-60-6.mol

Synonyms:

Chemical Property of N-[(benzyloxy)carbonyl]alanylthreonine

Chemical Property:

• Vapor Pressure: 1.59E-16mmHg at 25°C
• Boiling Point: 625.8°C at 760 mmHg
• Flash Point: 332.3°C
• Density: 1.3g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[(benzyloxy)carbonyl]alanylthreonine

There total 9 articles about N-[(benzyloxy)carbonyl]alanylthreonine 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: 88.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate (820239-42-7) → (2S,3R)-2-((S)-2-(((benzyl)oxycarbonyl)amino)propanamido)-3-hydroxybutanoic acid (78609-60-6)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2015.05.020

Reference yield:

O-(((benzyloxy)carbonyl)-L-alanyl)-L-threonine hydrochloride → C26H31N3O9 + Z-Ala-Thr-OH (40355-98-4,40356-04-5,55057-57-3,78609-60-6,109718-19-6)

Guidance literature:

In aq. phosphate buffer; at 50 ℃; for 3h; pH=7.4; Microwave irradiation;

DOI:10.3998/ark.5550190.p008.796

Reference yield:

N-Cbz-Ala (1142-20-7) → (2S,3R)-2-((S)-2-(((benzyl)oxycarbonyl)amino)propanamido)-3-hydroxybutanoic acid (78609-60-6)

Guidance literature:

With tetrahydrofuran; chloroformic acid ethyl ester; triethylamine; anschliessend Behandeln mit L_s-Threonin und wss. NaOH;

upstream raw materials:

N-benzyloxycarbonylalanine

N-Cbz-Ala

L-threonine

(N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester

Downstream raw materials:

(S)-2-[(S)-2-(2-{(S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionylamino]-propionylamino}-acetylamino)-propionylamino]-3-hydroxy-butyric acid

Ala-Thr

N-[N-(N-benzyloxycarbonyl-L-alanyl)-L_S-threonyl]-L-cysteine

Refernces

• 1、 Panda, Siva S.,Liaqat, Sumaira,Tiwari, Anand D.,Marwani, Hadi M.,Faidallah, Hassan M.,Rauf, Abdul,Hall, C. Dennis,Katritzky, Alan R.. "Ligations of O-acyl threonine units to give native peptides via 5-, 8-, 9- and 10-membered cyclic transition states". . p. 9 - 18. Retrieved 2015/03/03.
• 2、 Kawasaki, Koichi,Maeda, Mitsuko,Tamura, Hiromi,Ohashi, Sumiko,Yoshimura, Tetsuhiko,Hatayama Etsuji et al.. "Amino Acids and Peptides. III. Synthesis of Model Peptides Related to Cytochrome P-450". . p. 1717 - 1723. Retrieved 2007/10/02.