Boc-D-glu-ome

Base Information

• Chemical Name: Boc-D-glu-ome
• CAS No.: 55227-00-4
• Molecular Formula: C11H19 N O6
• Molecular Weight: 261.275
• Hs Code.: 2924199090
• European Community (EC) Number: 816-993-6
• DSSTox Substance ID: DTXSID00427016
• Wikidata: Q72510185
• Mol file: 55227-00-4.mol

Synonyms:BOC-D-GLU-OME;55227-00-4;(4R)-5-methoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;(R)-4-((tert-Butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid;N-tert-Butoxycarbonyl-D-glutamic acid 1-methyl ester;SCHEMBL6409351;DTXSID00427016;MFCD00076930;AKOS015850963;FD21409;AS-49058;CS-0169313;EN300-1589423;N-alpha-t-Butyloxycarbonyl-D-glutamic acid methyl ester;(R)-4-(tert-butoxycarbonylamino)-5-methoxy-5-oxopentanoic acid;(4R)-4-{[(tert-butoxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acid

Chemical Property of Boc-D-glu-ome

Chemical Property:

• Boiling Point: 428.4±40.0 °C(Predicted)
• PKA: 4.48±0.10(Predicted)
• PSA: 101.93000
• Density: 1.182
• LogP: 1.30840
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 261.12123733
• Heavy Atom Count: 18
• Complexity: 320

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-D-Glu-OMe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Boc-D-glu-ome

There total 1 articles about Boc-D-glu-ome 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:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester (55227-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / dimethylformamide

2: 35 g / H₂ / Pd/C / ethanol

With hydrogen; potassium carbonate; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b702649h

Reference yield: 83.0%

α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester (55227-00-4) + (2R,3S)-3-Benzyloxy-2-methylamino-butyric acid benzyl ester; compound with trifluoro-acetic acid → (2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester (474085-50-2)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ja0206700

Reference yield: 75.0%

α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester (55227-00-4) + (S)-2-[(R)-2-(2-Cyclohexylamino-acetylamino)-propionylamino]-4-methyl-pentanoic acid tert-butyl ester → Boc-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-OtBu (225780-82-5)

Guidance literature:

With 2,3,5-trimethyl-pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; 1.) 0 deg C, 2 h, 2.) room temperature, 10 h;

DOI:10.1016/S0968-0896(98)00254-5

upstream raw materials:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid

Downstream raw materials:

(R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid

(R)-4-(Benzyloxycarbonylmethyl-methyl-carbamoyl)-2-tert-butoxycarbonylamino-butyric acid methyl ester

Boc-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-OtBu

(2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester

Refernces

• 1、 Cluzeau, Jerome,Oishi, Shinya,Ohno, Hiroaki,Wang, Zixuan,Evans, Barry,Peiper, Stephen C.,Fujii, Nobutaka. "Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists". . p. 1915 - 1923. Retrieved 2008/02/10.
• 2、 Mehrotra, Amit P.,Webster, Kerri L.,Gani, David. "Design and preparation of serine-threonine protein phosphatase inhibitors based upon the nodularin and microcystin toxin structures: Part 1. Evaluation of key inhibitory features and synthesis of a rationally stripped-down nodularin macrocycle". . p. 2495 - 2511. Retrieved 2007/10/03.