158478-76-3

Basic information

• Product Name: 1 3-DI-BOC-2-(CARBOXYMETHYL)GUANIDINE
• Synonyms: N-[N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]glycine
• CAS NO: 158478-76-3
• Molecular Formula: C₁₃H₂₃N₃O₆
• Molecular Weight: 317.34
• Mol File: 158478-76-3.mol

Chemical Properties

• Appearance: /
• Density: 1.2g/cm³
• Refractive Index: 1.501
• CAS DataBase Reference: 1 3-DI-BOC-2-(CARBOXYMETHYL)GUANIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 3-DI-BOC-2-(CARBOXYMETHYL)GUANIDINE(158478-76-3)
• EPA Substance Registry System: 1 3-DI-BOC-2-(CARBOXYMETHYL)GUANIDINE(158478-76-3)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 158478-76-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Di-BOC-2-(Carboxymethyl)guanidine is used as a key intermediate in the synthesis of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4. These antagonists play a crucial role in modulating the immune response and have potential applications in the treatment of various diseases, including autoimmune disorders, inflammatory conditions, and certain types of cancer.
Organic Synthesis:
In the field of organic synthesis, 1,3-Di-BOC-2-(Carboxymethyl)guanidine serves as a valuable building block for the creation of complex molecular structures. Its unique chemical properties enable the formation of a wide range of bioactive compounds, making it an essential component in the development of new drugs and therapeutic agents.

InChI:InChI=1/C13H23N3O6/c1-12(2,3)21-10(19)15-9(14-7-8(17)18)16-11(20)22-13(4,5)6/h7H2,1-6H3,(H,17,18)(H2,14,15,16,19,20)

Upstream product

• 1000312-21-9 methyl (N,N'-bis(tert-butoxycarbonyl)carbamimidoyl)glycinate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 207725-91-5 ethyl 2-(N,N'-bis(tert-butyloxycarbonyl)guanidino)ethanoate 
• 152120-54-2 N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine 
• 56-40-6 glycine 
• 145013-05-4 tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate 

Downstream Products

• 1000312-29-7 C₁₉H₃₄N₄O₅ 

Relevant articles and documents

Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)

Structure-activity relationship studies of the cyclopentapeptide CXCR4 antagonists (cyclo(-l-/d-Arg1-Arg2-2-Nal 3-Gly4-d-Tyr5-)) suggest that the l-/d-Arg 1-Arg2-2-Nal3/sup

Synthetic receptors for the differentiation of phosphorylated peptides with nanomolar affinities

Artificial ditopic receptors for the differentiation of phosphorylated peptides varying in i + 3 amino acid side chains were synthesized, and their binding affinities and selectivities were determined. The synthetic receptors show the highest binding affi

Convergent and stereospecific synthesis of molecules containing α-functionalized guanidiniums via α-guanidino acids

(Chemical Equation Presented) To introduce chirality and functional groups adjacent to guanidiniums to modulate specificity and affinity in recognition, N,N′-bis(Boc)-α-guanidino acids were synthesized from α-amino acid methyl esters. Protected α-guanidino acids coupled to cyclohexylamine and trans-1,4-diaminocyclohexane in good yield and with retention of stereochemistry. Boc deprotection was conducted under mild acidic conditions (0.5 M HCl/EtOAc) to minimize epimerization. The deprotected guanidinium is configurationally stable under more acidic conditions. This approach represents a practical, convergent, stereospecific methodology to introduce chiral α-substituted guanidinium groups into molecules.

A Constrained Diketopiperazine as a New Scaffold for the Synthesis of Peptidomimetics

As a new scaffold for peptidomimetic synthesis, a highly constrained bifunctional diketopiperazine, 4, has been prepared by smooth N-alkylation with tert-butyl bromoacetate. As a first application, we describe herein the synthesis of new peptidomimetics of the Arg-Gly-Asp (RGD) sequence. The product 30, which shows a selective platelet-aggregation inhibiting activity, can be used as a lead for the preparation of more potent products.

A convenient preparation of monosubstituted N,N'-di(Boc)-protected guanidines

1-H-Pyrazole-1-[N,N'-bis(tert-butoxycarbonyl)]carboxamidine (1) reacts under mild conditions with a number of amines and amino acids to give the respective protected guanidines in moderate to high isolated yields.