Boc-D-glutamic acid

Base Information

• Chemical Name: Boc-D-glutamic acid
• CAS No.: 34404-28-9
• Molecular Formula: C10H17NO6
• Molecular Weight: 247.248
• Hs Code.: 29225090
• European Community (EC) Number: 837-676-9
• DSSTox Substance ID: DTXSID90427060
• Nikkaji Number: J761.229J
• Wikidata: Q72449382
• Mol file: 34404-28-9.mol

Synonyms:34404-28-9;Boc-D-Glu-OH;Boc-D-glutamic acid;(R)-2-((tert-Butoxycarbonyl)amino)pentanedioic acid;N-(tert-Butoxycarbonyl)-D-glutamic Acid;Boc-L-Glu-OH;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid;D-Glutamic acid, N-[(1,1-dimethylethoxy)carbonyl]-;N-Boc-D-glutamic Acid;SCHEMBL1318658;DTXSID90427060;AQTUACKQXJNHFQ-ZCFIWIBFSA-N;MFCD00190790;AKOS022177941;AM81693;FD21394;HY-W039449;AC-17128;AC-24109;AC-24111;DS-13385;B2987;CS-0097294;EN300-147630;(R)-2-(tert-butoxycarbonylamino)pentanedioic acid;A847898;(R)-2-((tert-Butoxycarbonyl)amino)pentanedioicacid;Q-101678;(2R)-2-{[(tert-butoxy)carbonyl]amino}pentanedioic acid

Chemical Property of Boc-D-glutamic acid

Chemical Property:

• Melting Point: 108 °C(dec.)
• Refractive Index: 14 ° (C=1, MeOH)
• Boiling Point: 435.9 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 217.4 °C
• PSA: 112.93000
• Density: 1.264 g/cm³
• LogP: 1.22000
• Storage Temp.: Store at RT.
• Water Solubility.: Soluble in water
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 247.10558726
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

99%, ^*data from raw suppliers

Boc-D-glu-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CCC(=O)O)C(=O)O
• Uses: N-Boc-D-glutamic Acid is an N-Boc-protected form of D-Glutamic acid (G596965). D-Glutamic acid is an unnatural isomer of L-Glutamic acid (G596960), and is found in bacterial cell wall peptidoglycan of gram-positive and gram-negative bacteria. D-Glutamic acid also occurs as poly-gamma-Glutamic acid, which is a weak immunogen but is capable of acting as a hapten (a small molecule that induces the production of antibodies, as well as binding to them).

Technology Process of Boc-D-glutamic acid

There total 8 articles about Boc-D-glutamic 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: 100.0%

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + di-tert-butyl dicarbonate (24424-99-5) → N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid (34404-28-9)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 1h;

DOI:10.1021/ja209018u

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + D-glutamic acid hydrochloride (617-61-8) → N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid (34404-28-9)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 5h; Yield given; Irradiation;

DOI:10.1016/S0957-4166(98)00169-4

Reference yield:

t-butoxycarbonyl-D-glutamic acid γ-methyl ester dicyclohexylamine salt (76379-02-7) + S-Benzyl-L-Cys-Na-Salz → N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid (34404-28-9) + (R)-4-((R)-2-Benzylsulfanyl-1-carboxy-ethylcarbamoyl)-2-tert-butoxycarbonylamino-butyric acid

Guidance literature:

With phosphoric acid; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) MeOH, 10 kbar, 40 deg C, 10 d;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

l(-)-glutamic acid

D-Glutamic acid

tert-Butyl 4-nitrophenyl carbonate

Downstream raw materials:

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

(R)-7-chloro-4-<<1'-(chloromethyl)-4'-(diethylamino)butyl>amino>quinoline dihydrochloride

(R)-7-chloro-4-<<1'-(hydroxymethyl)-4'-(diethylamino)butyl>amino>quinoline

N-(tert-butoxycarbonyl)-D-glutamic diamide

Refernces

• 1、 De Cat, Inge,Gobbo, Cristian,Van Averbeke, Bernard,Lazzaroni, Roberto,De Feyter, Steven,Van Esch, Jan. "Controlling the position of functional groups at the liquid/solid interface: Impact of molecular symmetry and chirality". supporting information; experimental part. p. 20942 - 20950. Retrieved 2012/02/13.
• 2、 Klaerner, Frank-Gerrit,Kalthof, Ulrike,Gante, Joachim. "Peptide Synthesis at High Pressure: Activation Volume of a Peptide Coupling, Synthesis of a Glutathione Derivative". . p. 359 - 364. Retrieved 2007/10/03.