158478-76-3 Usage
Description
1,3-Di-BOC-2-(Carboxymethyl)guanidine is an organic compound that serves as an essential intermediate in the synthesis of various biologically active molecules. It is characterized by its unique chemical structure, which includes a guanidine group and a carboxylated side chain, protected by BOC (tert-butyloxycarbonyl) groups. This structure allows it to be a versatile building block in the development of pharmaceuticals and other bioactive compounds.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 158478-76-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,4,7 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 158478-76:
(8*1)+(7*5)+(6*8)+(5*4)+(4*7)+(3*8)+(2*7)+(1*6)=183
183 % 10 = 3
So 158478-76-3 is a valid CAS Registry Number.
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)
158478-76-3Relevant articles and documents
Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)
Zachariassen, Zack G.,Thiele, Stefanie,Berg, Erik A.,Rasmussen, Pernille,Fossen, Torgils,Rosenkilde, Mette M.,V?ben?, Jon,Haug, Bengt Erik
, p. 4759 - 4769 (2014)
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
Convergent and stereospecific synthesis of molecules containing α-functionalized guanidiniums via α-guanidino acids
Balakrishnan, Shalini,Zhao, Chen,Zondlo, Neal J.
, p. 9834 - 9837 (2008/09/16)
(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 convenient preparation of monosubstituted N,N'-di(Boc)-protected guanidines
Drake,Patek,Lebl
, p. 579 - 582 (2007/10/02)
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.
