24757-70-8

Basic information

• Product Name: CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE)
• Synonyms: CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE);2-Methoxy-6-amino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine;9-(2-Deoxy-beta-D-ribofuranosyl)-2-methoxyadenine;Cladribine USP Related Compound A;Cladribine Impurity B
• CAS NO: 24757-70-8
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.2679
• Mol File: 24757-70-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 659.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.84±0.1 g/cm3(Predicted)
• PKA: 13.77±0.60(Predicted)
• CAS DataBase Reference: CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE)(CAS DataBase Reference)
• NIST Chemistry Reference: CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE)(24757-70-8)
• EPA Substance Registry System: CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE)(24757-70-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 24757-70-8(Hazardous Substances Data)

Usage

Description

CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE) is an impurity found in the synthesis of Cladribine (M262330), a substituted purine nucleoside with antileukemic activity.

Uses

Used in Pharmaceutical Industry:
CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE) is used as an impurity in the synthesis of Cladribine, a medication with antileukemic properties. CLADRIBINE RELATED COMPOUND A (20 MG) (2-METHOXY-2'-DEOXYADENOSINE) plays a role in the production process of Cladribine, which is utilized for the treatment of various types of leukemia and lymphoma.

Upstream product

• 67-56-1 methanol 
• 89178-21-2 2-bromo-2′-deoxyadenosine 
• 124-41-4 sodium methylate 
• 4291-63-8 2-chloro-2'-deoxyadenosine 
• 512-56-1 trimethyl phosphite 
• 106449-56-3 2'-deoxyisoguanosine 

Downstream Products

• 28128-30-5 2-methoxy-9H-purin-6-amine 

Relevant articles and documents

Substituent reactivity and tautomerism of isoguanosine and related nucleosides

The substituent reactivity and tautomerism of isoguanine nucleosides is studied. Benzoylation or tosylation of isoguanine nucleosides (pyridine, room temperature) yields the 2-benzoyl derivatives 7c, 11, and 12 or the 2-tosyl compounds 13 and 14. The isobutyrylation of the 6-amino group which did not occur under these conditions was induced in the presence of Me3SiCl. In the absence of Me3SiCl, the reactivity of isoguanine substituents decreases in the order from 2-oxo → 5'-OH → 3'-OH → 6-NH2. From isoguanine nucleosides, the N1-(2b),N3-(17),N6-(15a,b), and 2-O-alkylated (3b) derivatives were prepared. Their pK(a) values were determined and the UV and 13C-NMR spectra compared with regard to the alkylation position. Also the tautomeric forms of isoguanine nucleosides were determined UV-spectrophotometrically in aqueous and nonaqueous solution. Isoguanosine (1a), its 2'-deoxy analogue 1b as well as the N6-methyl- and 8-substituted derivatives form lactam tautomers in aqueous solution, whereas the lactim form is present in dioxane.

Characterization of cladribine and its related compounds by high- performance liquid chromatography/mass spectrometry

High-performance liquid chromatography/mass spectrometer (HPLC/MS) was used to identify and structurally characterize the modified nucleoside cladribine (2-chloro-2'-deoxy-β-adenosine) and 13 synthesis-related byproducts in bulk drug. Confirmation of compound identity was accomplished by spectral analysis (1H and 13C NMR spectroscopy, mass spectrometry, and UV absorption spectroscopy) of the related compounds as isolated from crude mixtures of the drug substance and by spiking experiments with authentic standards. The use of on-line mass spectrometric analysis (i.e., LC/MS) to augment UV absorption spectra permitted rapid identification of many of the compounds of interest.