z-d-Glu-ome

Base Information

• Chemical Name: z-d-Glu-ome
• CAS No.: 26566-11-0
• Molecular Formula: C14H17NO6
• Molecular Weight: 295.289
• DSSTox Substance ID: DTXSID00426423
• Nikkaji Number: J1.161.588K
• Wikidata: Q72502167
• Mol file: 26566-11-0.mol

Synonyms:z-d-glu-ome;26566-11-0;(4R)-5-methoxy-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid;(R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid;SCHEMBL2777678;DTXSID00426423;MFCD00798654;FD21462;AS-49079;CS-0129470;EN300-7374620;A877189;1-methyl N-benzyloxycarbonyl-D-glutamate;N-(Benzyloxycarbonyl)-D-glutamic acid 1-methyl ester;D-Glutamic acid,N-[(phenylmethoxy)carbonyl]-,1-methyl ester;(R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoicacid;(4R)-4-{[(BENZYLOXY)CARBONYL]AMINO}-5-METHOXY-5-OXOPENTANOIC ACID

Chemical Property of z-d-Glu-ome

Chemical Property:

• Vapor Pressure: 3.01E-11mmHg at 25°C
• Refractive Index: 1.535
• Boiling Point: 510.6 °C at 760 mmHg
• PKA: 4.48±0.10(Predicted)
• Flash Point: 262.6 °C
• PSA: 101.93000
• Density: 1.272 g/cm³
• LogP: 1.71010
• Storage Temp.: Store at 0°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 295.10558726
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

99%+, ^*data from raw suppliers

Z-D-Glu-ome ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CCC(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: COC(=O)[C@@H](CCC(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of z-d-Glu-ome

There total 9 articles about z-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: 100.0%

N-Cbz-D-glutamic acid 5-allyl-1-methyl ester → N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester (26566-11-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane; In dichloromethane; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/chem.201604279

Reference yield: 93.0%

methanol (67-56-1) + (4R)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one (97975-57-0) → N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester (26566-11-0)

Guidance literature:

With sodium methylate;

DOI:10.1016/j.tet.2004.07.080

Reference yield:

N-(benzyloxycarbonyl)-D-glutamic acid 5-tert-butyl ester 1-methyl ester (56877-41-9) → Z-L-GluOMe (5672-83-3) + N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester (26566-11-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1039/b514583j

upstream raw materials:

N-benzyloxycarbonyl-D-glutamic acid

dimethyl sulfate

methanol

(4R)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one

Downstream raw materials:

7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6S)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

methyl [7-methyl (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate

Refernces

• 1、 Van Heerbeek, Rieko,Kamer, Paul C. J.,Van Leeuwen, Piet N.M.W.,Reek, Joost N.H.. "Synthesis of carbosilane dendritic wedges and their use for the construction of dendritic receptors". . p. 211 - 223. Retrieved 2007/10/03.