181475-59-2

Basic information

• Product Name: 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine
• Synonyms: 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine
• CAS NO: 181475-59-2
• Molecular Weight: 486.527
• Mol File: 181475-59-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine(181475-59-2)
• EPA Substance Registry System: 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine(181475-59-2)

Safety Data

• Hazardous Substances Data: 181475-59-2(Hazardous Substances Data)

Upstream product

• 91713-46-1 6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine 
• 18815-74-2 zinc methyl bromide 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 2004-03-7 6-methylpurine 

Downstream Products

• 16006-64-7 6-methyl-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 

Relevant articles and documents

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.

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.