152120-54-2

Basic information

• Product Name: N,N'-BIS-BOC-1-GUANYLPYRAZOLE
• Synonyms: N,N'-BIS-(T-BUTYL-OXYCARBONYL)-1-GUANYLPYRAZOLE;N,N'-BIS-BOC-1-GUANYLPYRAZOLE;N,N'-BIS-(TERT-BUTYLOXYCARBONYL)-1-GUANYLPYRAZOLE;PYRAZOLE(BOC)2;PYRAZOL(BOC)2;N,N''-Bis-(tert-butoxycarbonyl)-1-guanylpyrazole;N,N'-DiBoc-1H-Pyrazole Guanidine;N,N-Bis-(t-butyloxycarbonyl)-1-guanylpyrazole, N,N-Di-Boc-1H-pyrazole-1-carboxamidine
• CAS NO: 152120-54-2
• Molecular Formula: C₁₄H₂₂N₄O₄
• Molecular Weight: 310.35
• Product Categories: Guanidine Protection/Guanidinylation;Peptide Synthesis;Specialty Synthesis
• Mol File: 152120-54-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 86-90 °C(lit.)
• Appearance: /
• Density: 1.16 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slghtly), Methanol (Slightly)
• PKA: 6.92±0.46(Predicted)
• Water Solubility: Slightly soluble in water. Soluble in methanol, and chloroform.
• CAS DataBase Reference: N,N'-BIS-BOC-1-GUANYLPYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-BIS-BOC-1-GUANYLPYRAZOLE(152120-54-2)
• EPA Substance Registry System: N,N'-BIS-BOC-1-GUANYLPYRAZOLE(152120-54-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 152120-54-2(Hazardous Substances Data)

Usage

Description

N,N'-BIS-BOC-1-GUANYLPYRAZOLE, also known as N,N'-Di-Boc-1H-pyrazole-1-carboxamidine or Bis-Boc-pyrazolocarboxamidine (Pyrazol(BOC)2), is a white solid compound commonly utilized as a guanidinylating reagent in organic synthesis. It plays a crucial role in the stereoselective synthesis of various bicyclic guanidine alkaloids, such as (+)-monanchorin.

Uses

Used in Pharmaceutical Industry:
N,N'-BIS-BOC-1-GUANYLPYRAZOLE is used as a guanidinylating reagent for the stereoselective synthesis of bicyclic guanidine alkaloids, such as (+)-monanchorin. This application is significant in the development of new pharmaceutical compounds with potential therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, N,N'-BIS-BOC-1-GUANYLPYRAZOLE serves as an essential reagent for the synthesis of complex organic molecules, particularly those containing guanidine functional groups. Its use in this industry is vital for the creation of novel chemical entities with potential applications in various sectors, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 152120-61-1 tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate 
• 152120-61-1 tert-butyl (amino(1H-pyrazol-1-yl)methylene)carbamate 
• 313983-06-1 tert-butyl tert-butoxycarbonyl(((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)carbamate 
• 4023-02-3 1H-pyrazole-1-carboximidamide hydrochloride 
• 4023-00-1 1H-Pyrazole-1-carboxamidine 

Downstream Products

• 158478-76-3 (N,N'-bis(tert-butoxycarbonyl)carbamimidoyl)glycine 
• 333406-04-5 (5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-(2R)-2-(3-N,N'-bis-t-boc-guanidino-propyl)-6-phenyl-hexanoic acid 
• 714275-86-2 C₂₃H₂₉N₃O₅ 
• 245116-21-6 C₂₈H₃₆ClN₃O₈ 
• 741697-32-5 C₂₉H₃₉N₃O₈ 

Relevant articles and documents

Synthesis and characterization of 4(R)-epimer impurities of zanamivir and laninamivir octanoate

The synthesis and characterization of compounds 7c and 8d, the 4(R)-epimer impurities of zanamivir and laninamivir octanoate, were reported for the first time. Their structures were confirmed by NMR and MS and distinguished from their corresponding active pharmaceutical ingredient (API) by coupling constant in 1H NMR and HPLC spectra. This work is of great significance for the drug-related substances analysis in zanamivir and laninamivir octanoate.

RADIOIODINATED COMPOUNDS

This disclosure relates to reagents and methods useful in the synthesis of aryl iodines, for example, in the preparation of iodine labeled radiotracers. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.

Structure-activity relationship study on α1 adrenergic receptor antagonists from beer

Hordatine A and aperidine have been previously isolated from beer as active ingredients, which bind to muscarinic M3 receptor. In addition, these compounds have exhibited antagonist activity against the α1A adrenoceptor. Although the relative structures of these two molecules have previously been determined, the absolute stereochemistry was unclear. Hence, to elucidate the absolute stereochemistry of natural hordatine A, we synthesized each enantiomer of hordatine A and aperidine from optically pure dehydrodi-p-coumaric acid. Several additional related compounds were also synthesized for structure-activity relationship studies. Chiral column HPLC analysis demonstrated that the absolute stereochemistry of natural hordatine A is (2S,3S), while based on the isomerization mechanism, the stereochemistry of aperidine is (2R,3S). The α1A adrenoceptor binding activity of (2R,3R)-hordatine A is the most potent among the enantiomeric pairs of hordatines and aperidines. Furthermore, the related, synthetic compound, (2R,3R)-methyl benzofurancarboxylate exhibits antagonist activity against the α1A adrenoceptor at a lower concentration than that of hordatine A.