BOC-ALA-D-GLU(OBZL)-NH2

Base Information

• Chemical Name: BOC-ALA-D-GLU(OBZL)-NH2
• CAS No.: 18814-49-8
• Molecular Formula: C20H29 N3 O6
• Molecular Weight: 407.467
• Hs Code.: 2924190090
• Mol file: 18814-49-8.mol

Synonyms:D-a-Glutamine,N2-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-, phenylmethyl ester; Glutaramicacid, 4-[2-(carboxyamino)propionamido]-, 1-benzyl tert-butyl ester, D- (8CI)

Chemical Property of BOC-ALA-D-GLU(OBZL)-NH2

Chemical Property:

• Melting Point: 133-134℃
• Boiling Point: 664.2±55.0 °C(Predicted)
• PKA: 11.33±0.46(Predicted)
• PSA: 136.82000
• Density: 1.185±0.06 g/cm3(Predicted)
• LogP: 2.87540
• Storage Temp.: -15°C

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-Ala-D-Glu(OBzl)-NH2 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-ALA-D-GLU(OBZL)-NH2

There total 30 articles about BOC-ALA-D-GLU(OBZL)-NH2 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: 95.0%

D-Glutaminsaeure-α-amid-γ-benzylester (71811-14-8,80064-48-8) + Boc-Ala-O-N-hydroxysuccinimide (3392-05-0) → tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester (18814-49-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1021/acs.joc.0c01852

Reference yield: 83.0%

γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate (53759-36-7) → tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester (18814-49-8)

Guidance literature:

With ammonium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In acetonitrile; for 1h;

DOI:10.1007/BF02249692

Reference yield: 81.0%

L-N-Boc-Ala (15761-38-3) + (R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-aminium 2,2,2-trifluoroacetate (80143-17-5) → tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester (18814-49-8)

Guidance literature:

L-N-Boc-Ala; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; for 0.5h;

(R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-aminium 2,2,2-trifluoroacetate; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 15h;

upstream raw materials:

L-N-Boc-Ala

D-γ-methyl isoglutamine hydrochloride

γ-benzyl isoglutaminate perchlorate

benzyl bromide

Downstream raw materials:

L-alanyl-D-isoglutamine benzyl ester hydrochloride

L-alanyl-D-isoglutamine benzyl ester trifluoroacetate

muramyl dipeptide

L-alanyl-D-isoglutamine

Refernces

• 1、 Mashayekh, Siavash,Bersch, Klare L.,Ramsey, Jared,Harmon, Thomas,Prather, Benjamin,Genova, Lauren A.,Grimes, Catherine L.. "Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments". supporting information. p. 16243 - 16253. Retrieved 2020/11/13.
• 2、 Cheng, Wei-Chieh,You, Ting-Yun,Teo, Zhen-Zhuo,Sayyad, Ashik A.,Maharana, Jitendra,Guo, Chih-Wei,Liang, Pi-Hui,Lin, Chung-Shun,Meng, Fan-Chun. "Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity". . p. 3836 - 3844. Retrieved 2020/10/21.