N-Boc-3-azido-L-alanine

Base Information

• Chemical Name: N-Boc-3-azido-L-alanine
• CAS No.: 122225-54-1
• Molecular Formula: C₈H₁₄N₄O₄
• Molecular Weight: 230.224
• Hs Code.: 9999999999
• European Community (EC) Number: 846-236-5
• Nikkaji Number: J2.867.887H
• Mol file: 122225-54-1.mol

Synonyms:122225-54-1;N-Boc-3-azido-L-alanine;N-TERT-BUTOXYCARBONYL-AZIDO-L-ALANINE;SCHEMBL13483252;KIFVOLVBGXELHT-YFKPBYRVSA-N;AKOS030212203;N-(tert-Butoxycarbonyl)-3-azido-L-alanine;F79093;EN300-1717211;3-?Azido-?N-?[(1,?1-?dimethylethoxy)?carbonyl]?-?L-?alanine

Chemical Property of N-Boc-3-azido-L-alanine

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 230.10150494
• Heavy Atom Count: 16
• Complexity: 317

Purity/Quality:

98.5% ^*data from raw suppliers

Na-Boc-Nb-azido-L-2,3-diaminopropionicacidcyclohexylammoniumsalt,≥99%(HPLC) ≥99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CN=[N+]=[N-])C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CN=[N+]=[N-])C(=O)O

Technology Process of N-Boc-3-azido-L-alanine

There total 15 articles about N-Boc-3-azido-L-alanine 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: 98.0%

(S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate (97651-96-2) → (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid (122225-54-1,108283-49-4)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/jacs.7b06144

Reference yield: 90.0%

[2-azido-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester → (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid (122225-54-1,108283-49-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran;

DOI:10.1055/s-2004-817770

Reference yield: 89.0%

(S)-tert-butyl (3-azido-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (684270-37-9) → (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid (122225-54-1,108283-49-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.11.017

upstream raw materials:

(S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate

(2S)-3-azido-2-tert-butoxycarbonylamino-propan-1-ol

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(4S)-4-azidomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate

benzyl (2S)-3-azido-2-[(tert-butoxycarbonyl)amino]propanoate

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid

L-azidoalanine hydrochloride

Refernces

• 1、 Liu, Chao,Chen, Xiao,Zhi, Xin,Weng, Weizong,Li, Quan,Li, Xiang,Zou, Yan,Su, Jiacan,Hu, Hong-Gang. "Structure-based development of an osteoprotegerin-like glycopeptide that blocks RANKL/RANK interactions and reduces ovariectomy-induced bone loss in mice". . p. 661 - 672. Retrieved 2018/01/19.
• 2、 Guo, Ye,Liu, Chao,Song, Hui,Wang, Feng-Liang,Zou, Yan,Wu, Qiu-Ye,Hu, Hong-Gang. "Diaminodiacid-based synthesis of macrocyclic peptides using 1,2,3-triazole bridges as disulfide bond mimetics". . p. 2110 - 2114. Retrieved 2017/01/21.