16006-64-7

Basic information

• Product Name: 6-methylpurine 2'-deoxyriboside
• Synonyms: 6-methylpurine 2'-deoxyriboside;9-(2-Deoxy-β-D-erythropentofuranosyl)-6-methyl-9H-purine;6-METHYLPURINE-2-DEOXY-BETA-D-RIBOSIDE
• CAS NO: 16006-64-7
• Molecular Formula: C₁₁H₁₄N₄O₃
• Molecular Weight: 250.257
• Mol File: 16006-64-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 544.7°Cat760mmHg
• Flash Point: 283.2°C
• Appearance: /
• Density: 1.67g/cm³
• CAS DataBase Reference: 6-methylpurine 2'-deoxyriboside(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methylpurine 2'-deoxyriboside(16006-64-7)
• EPA Substance Registry System: 6-methylpurine 2'-deoxyriboside(16006-64-7)

Safety Data

• Hazardous Substances Data: 16006-64-7(Hazardous Substances Data)

Usage

General Description

6-methylpurine 2'-deoxyriboside is a chemical compound that consists of a 6-methylpurine base attached to a 2'-deoxyribose sugar molecule. It is a nucleoside, which means it is a building block of nucleic acids like DNA and RNA. 6-methylpurine 2'-deoxyriboside is an important intermediate in the biosynthesis of certain modified nucleosides in DNA. It is also used in some research studies as a model compound for investigating the chemical behavior and reactivity of similar nucleosides. Additionally, 6-methylpurine 2'-deoxyriboside has been investigated for its potential biological and therapeutic activities, including its role in promoting cell growth and its potential use in cancer treatment. Overall, this compound has significant relevance in both biological and chemical research.

Upstream product

• 20289-65-0 9-(3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl)-6-methylpurine 
• 156517-72-5 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine 
• 17318-24-0 3',5'-di-O-acetyl-2'-deoxyadenosine 
• 890-38-0 2-deoxyinosine 
• 2004-03-7 6-methylpurine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 215372-43-3 Thiocarbonic acid O-phenyl ester O-[(2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester 
• 215372-40-0 Acetic acid (2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 215372-42-2 (2R,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 182195-43-3 2'-O-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)inosine 
• 87791-89-7 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)inosine 
• 91713-46-1 6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine 
• 52162-55-7 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride 
• 215372-44-4 9-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl)-1,3-disiloxanediyl-β-D-erythro-pentoribofuranosyl]-6-methylpurine 

Downstream Products

• 17039-17-7 2-deoxy–α-D-ribose 1-phosphate 
• 2004-03-7 6-methylpurine 

Relevant articles and documents

Analogs of 6-methyl-9-beta-D-ribofuranosylpurine.

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Stereoselective synthesis of 6-methyl-9-(2-deoxy-β-D-erythro- pentofuranosyl)purine

The coupling of the sodium salt of 6-methylpurine with 2-deoxy-3,5-di- O-p-toluoyl-α-D-erythro-pentofuranosyl chloride in acetonitrile gives the di-O-p-toluoyl protected 9-β nucleoside regio- and stereo-selectively in good yield. Methoxide deprotection followed by preparative hplc then affords pure 6-methyl-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine.

Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2’-DeoxyribosylTransferase from Trypanosoma brucei

The use of enzymes for the synthesis of nucleoside analogues offers several advantages over multistep chemical methods, including chemo-, regio- and stereoselectivity as well as milder reaction conditions. Herein, the production, characterization and utilization of a purine nucleoside 2’-deoxyribosyltransferase (PDT) from Trypanosoma brucei are reported. TbPDT is a dimer which displays not only excellent activity and stability over a broad range of temperatures (50–70 °C), pH (4–7) and ionic strength (0–500 mM NaCl) but also an unusual high stability under alkaline conditions (pH 8–10). TbPDT is shown to be proficient in the biosynthesis of numerous therapeutic nucleosides, including didanosine, vidarabine, cladribine, fludarabine and nelarabine. The structure-guided replacement of Val11 with either Ala or Ser resulted in variants with 2.8-fold greater activity. TbPDT was also covalently immobilized on glutaraldehyde-activated magnetic microspheres. MTbPDT3 was selected as the best derivative (4200 IU/g, activity recovery of 22 %), and could be easily recaptured and recycled for >25 reactions with negligible loss of activity. Finally, MTbPDT3 was successfully employed in the expedient synthesis of several nucleoside analogues. Taken together, our results support the notion that TbPDT has good potential as an industrial biocatalyst for the synthesis of a wide range of therapeutic nucleosides through an efficient and environmentally friendly methodology.

Convenient syntheses of 6-methylpurine and related nucleosides

Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-β-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)4Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis of 8, which is needed in significant amounts for studies in cancer gene therapy.