Cas no 19898-41-0 (H-D-Glu(OBzl)-OBzl p-tosylate)

H-D-Glu(OBzl)-OBzl p-tosylate is a protected derivative of glutamic acid, featuring benzyl ester groups at both the α-carboxyl and side-chain carboxyl functionalities, along with a p-tosylate counterion. This compound is primarily utilized in peptide synthesis, where its protective groups enhance selectivity during coupling reactions while minimizing side reactions. The p-tosylate salt form improves solubility in organic solvents, facilitating handling in solid-phase and solution-phase synthesis. Its stability under standard peptide coupling conditions makes it a reliable building block for constructing complex peptide structures. The benzyl ester groups can be selectively removed under mild hydrogenolysis conditions, allowing for controlled deprotection in multi-step syntheses.
H-D-Glu(OBzl)-OBzl p-tosylate structure
H-D-Glu(OBzl)-OBzl p-tosylate structure
Product Name:H-D-Glu(OBzl)-OBzl p-tosylate
CAS No:19898-41-0
MF:C26H29NO7S
MW:499.575966596603
MDL:MFCD00153435
CID:105676
PubChem ID:25185975
Update Time:2025-05-27

H-D-Glu(OBzl)-OBzl p-tosylate Chemical and Physical Properties

Names and Identifiers

    • H-D-GLU(OBZL)-OBZL TOS-OH
    • H-D-GLU(OBZL)-OBZL TOS
    • D-GLUTAMIC ACID(OBZL)-OBZL P-TOSYLATE
    • D-GLUTAMIC ACID GAMMA-BENZYL ESTER ALPHA-BENZYL ESTER TOSYLATE
    • D-GLUTAMIC ACID ALPHA,GAMMA-DIBENZYL ESTER 4-TOLUENESULFONATE SALT
    • D-GLUTAMIC ACID ALPHA,GAMMA-DIBENZYL ESTER P-TOLUENESULFONATE SALT
    • D-GLUTAMIC ACID-ALPHA,GAMMA-DIBENZYL ESTER P-TOSYLATE
    • D-(G-O-BZL)-GLU-OBZL TSOH
    • D-Glutamic acid dibenzyl ester 4-toluenesulfonate
    • H-D-Glu(Bzl)-OBzl*Tos
    • H-D-Glu(OBzl)-OBzl · p-tosylate
    • H-D-GLU(OBZL)-OBZL P-TOSYLATE
    • H-D-Glu(Obzl)-Obzl.HCl
    • H-D-Glu(OBzl)-OBzl.Tos
    • H-D-Glu(OBzl)-Obzl.TosOH
    • H-D-Glu(OBzl)-OBzl?Tos-OH
    • D-glutamate dibenzylester p-toluenesulfonate
    • D-glutamic acid dibenzyl ester p-toluenesufonate salt
    • D-glutamic acid dibenzyl ester p-toluenesulfonate
    • dibenzyl D-glutamate p-toluenesulfonate
    • dibenzyl D-glutamate p-toluenesulfonic acid salt
    • H-D-Glu(Bzl)OBzl * p-toluenesulphonic acid
    • D-Glutamic acid 1,5-bis(phenylmethyl) ester 4-methylbenzenesulfonate (1:1)
    • H-D-Glu(OBzl)-OBzl
    • D-Glu(OBzl)-OBzl·Tos
    • D-Glu(OBzl)-OBzl·TosOH
    • Dibenzyl D-glutamate tosylate
    • D-Glutamic acid di-benzyl ester tosylate
    • Q-101689
    • AKOS015842543
    • D-Glutamic acid, 1,5-bis(phenylmethyl) ester, 4-methylbenzenesulfonate (1:1)
    • FD21479
    • dibenzyl (2R)-2-aminopentanedioate;4-methylbenzenesulfonic acid
    • (R)-Dibenzyl 2-aminopentanedioate 4-methylbenzenesulfonate
    • D-Glutamic acid dibenzyl ester tosylate
    • H-D-GLU(OBZL)-OBZLP-TOSYLATE
    • 19898-41-0
    • H-D-Glu(OBzl)-OBzl. Tos
    • 4-Methylbenzene-1-sulfonic acid--dibenzyl D-glutamate (1/1)
    • AS-49087
    • SCHEMBL4692008
    • H-D-Glu(OBzl)-OBzl.Tos-OH
    • CS-0196957
    • A847902
    • 2-Amino-2,4-dibenzyl-pentanedioic acid; compound with toluene-4-sulfonic acid
    • C26H29NO7S
    • DTXSID70648978
    • MFCD00153435
    • 1,5-DIBENZYL (2R)-2-AMINOPENTANEDIOATE; PARA-TOLUENE SULFONATE
    • H-D-Glu(OBzl)-OBzl p-tosylate
    • MDL: MFCD00153435
    • Inchi: 1S/C19H21NO4.C7H8O3S/c20-17(19(22)24-14-16-9-5-2-6-10-16)11-12-18(21)23-13-15-7-3-1-4-8-15;1-6-2-4-7(5-3-6)11(8,9)10/h1-10,17H,11-14,20H2;2-5H,1H3,(H,8,9,10)/t17-;/m1./s1
    • InChI Key: HVZUAIVKRYGQRM-UNTBIKODSA-N
    • SMILES: S(C1C=CC(C)=CC=1)(=O)(=O)O.O(CC1C=CC=CC=1)C([C@@H](CCC(=O)OCC1C=CC=CC=1)N)=O

Computed Properties

  • Exact Mass: 499.16600
  • Monoisotopic Mass: 499.16647344g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 35
  • Rotatable Bond Count: 11
  • Complexity: 593
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 141?2

Experimental Properties

  • PSA: 141.37000
  • LogP: 5.60350

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Additional information on H-D-Glu(OBzl)-OBzl p-tosylate

Comprehensive Guide to H-D-Glu(OBzl)-OBzl p-tosylate (CAS No. 19898-41-0): Properties, Applications, and Industry Insights

H-D-Glu(OBzl)-OBzl p-tosylate (CAS No. 19898-41-0) is a specialized protected amino acid derivative widely utilized in peptide synthesis and pharmaceutical research. This compound, featuring benzyl (OBzl) protecting groups and a p-tosylate counterion, is critical for controlled reactions in organic chemistry. Its unique structure ensures stability during complex synthetic processes, making it a preferred choice for researchers exploring peptide-based therapeutics and drug discovery.

In recent years, the demand for custom peptide synthesis has surged due to advancements in biotechnology and personalized medicine. H-D-Glu(OBzl)-OBzl p-tosylate plays a pivotal role in this field, particularly in the development of targeted drug delivery systems and enzyme inhibitors. Researchers frequently search for "protected glutamate derivatives" or "OBzl group applications," highlighting its relevance in modern laboratories.

The compound’s solubility in organic solvents like DMF and DMSO facilitates its use in solid-phase peptide synthesis (SPPS), a technique dominating current peptide production. Its p-tosylate component enhances crystallinity, simplifying purification—a key concern for chemists optimizing "high-yield peptide coupling" methods. Discussions on platforms like ResearchGate often emphasize its utility in overcoming racemization challenges during asymmetric synthesis.

From an industrial perspective, CAS No. 19898-41-0 aligns with the growing focus on green chemistry. Manufacturers are innovating solvent-free activation protocols to reduce environmental impact, addressing queries like "sustainable peptide reagents." Analytical techniques such as HPLC and NMR confirm its high purity (>98%), a metric critical for compliance with pharmaceutical GMP standards.

Emerging trends in cancer research and neurodegenerative disease studies further elevate the importance of H-D-Glu(OBzl)-OBzl p-tosylate. Its role in constructing glutamate receptor modulators responds to frequent searches about "peptides for CNS disorders." The compound’s protecting group strategy also supports the synthesis of cyclic peptides, a hot topic in antibiotic development.

Storage recommendations for this compound typically suggest 2-8°C under inert gas, a detail often queried alongside "amino acid derivative stability." Suppliers increasingly provide COA (Certificate of Analysis) documentation, reflecting industry demands for traceable raw materials in preclinical trials.

In summary, H-D-Glu(OBzl)-OBzl p-tosylate (CAS No. 19898-41-0) bridges fundamental chemistry and cutting-edge applications. Its versatility in peptide engineering, combined with evolving synthetic methodologies, ensures its continued prominence in both academic and industrial settings. For researchers investigating "non-natural amino acid building blocks" or "orthogonal protection schemes," this compound remains indispensable.

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