(S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid

Base Information

• Chemical Name: (S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid
• CAS No.: 32991-17-6
• Molecular Formula: C13H24 N2 O5
• Molecular Weight: 288.344
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID70427023
• Nikkaji Number: J308.291A
• Wikidata: Q82239788
• Mol file: 32991-17-6.mol

Synonyms:32991-17-6;BOC-LEU-GLY-OH;(S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid;N-(tert-butoxycarbonyl)-L-leucylglycine;(tert-Butoxycarbonyl)-L-leucylglycine;N-t-butoxycarbonyl-leucyl-glycine;MFCD00076954;2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]acetic acid;2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanamido]acetic acid;Glycine, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-;SCHEMBL996962;DTXSID70427023;NRXDUMDULDHIEA-VIFPVBQESA-N;STL466238;AKOS005175183;DS-1419;HY-W039759;CS-0097840;EN300-303095;A875463;(S)-2-(2-(BOC-amino)-4-methylpentanamido)acetic acid;(S)-2-(2-(tert-butoxycarbonylamino)-4-methylpentanamido)acetic acid

Chemical Property of (S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid

Chemical Property:

• Boiling Point: 499.6±30.0 °C(Predicted)
• PKA: 3.42±0.10(Predicted)
• PSA: 104.73000
• Density: 1.122±0.06 g/cm3(Predicted)
• LogP: 1.90840
• Storage Temp.: -15°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 288.16852187
• Heavy Atom Count: 20
• Complexity: 360

Purity/Quality:

98%min ^*data from raw suppliers

Boc-Leu-Gly-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NCC(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H](C(=O)NCC(=O)O)NC(=O)OC(C)(C)C
• Uses: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-leucyl]-glycine is used to prepare aziridinedicarboxylic acid peptides as cysteine protease inhibitors. It is also used to prepare dipeptide monoester prodrugs of floxuridine with enhanced cancer cell growth inhibition.

Technology Process of (S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid

There total 11 articles about (S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid 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%

Boc-Leu-Gly-OAll (283176-66-9) → 2-((2S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetic acid (32991-17-6)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾;

DOI:10.1002/(SICI)1521-3773(20000417)39:8<1449::AID-ANIE1449>3.0.CO;2-A

Reference yield: 97.0%

Boc-L-Leu-Gly-OBzl (37783-45-2) → 2-((2S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetic acid (32991-17-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 18h;

DOI:10.1002/hlca.19940770424

Reference yield: 96.0%

(N-(tert-butoxycarbonyl)-L-leucinyl)glycine ethyl ester (51220-76-9) → 2-((2S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetic acid (32991-17-6)

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1246/bcsj.56.1527

upstream raw materials:

(N-(tert-butoxycarbonyl)-L-leucinyl)glycine ethyl ester

Boc-L-Leu-Gly-OBzl

Boc-Leu-ONSu

glycine

Refernces

• 1、 Awasthi, Satish Kumar,Raghothama, Srinivasa Rao,Balaram, Padmanabhan. "Conformational variability in short acyclic peptides. Stabilization of multiple ss-turn structures in organic solvents". . p. 2701 - 2706. Retrieved 1996.
• 2、 Zhang, Jian,Li, Xiaoyang,Jiang, Yuqi,Feng, Jinhong,Li, Xiaoguang,Zhang, Yingjie,Xu, Wenfang. "Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors". . p. 3055 - 3064. Retrieved 2014/05/20.
• 3、 Mou, Jiajia,Fang, Hao,Liu, Yingzi,Shang, Luqing,Wang, Qiang,Zhang, Lei,Xu, Wenfang. "Design, synthesis and primary activity assay of bi- or tri-peptide analogues with the scaffold l-arginine as amino-peptidase N/CD13 inhibitors". experimental part. p. 887 - 895. Retrieved 2010/05/02.