87791-33-1

Basic information

• Product Name: 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin
• CAS NO: 87791-33-1
• Molecular Weight: 567.709
• Mol File: 87791-33-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin(87791-33-1)
• EPA Substance Registry System: 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin(87791-33-1)

Safety Data

• Hazardous Substances Data: 87791-33-1(Hazardous Substances Data)

Upstream product

• 31598-80-8 2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose 
• 6958-73-2 4-(methylthio)-7H-pyrrolo<2,3-d>pyrimidine 
• 52492-40-7 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl bromide 

Downstream Products

• 87791-35-3 7-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 16754-83-9 7-(β-D-Arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 

Relevant articles and documents

ara-7-Deazanebularine - Synthesis of a Fluorescent Pyrrolopyrimidine Nucleoside by Phase-Transfer Glycosylation

ara-7-Deazanebularine (2b) and its 6-methylthio derivative 2a have been synthesized via phase-transfer glycosylation of 4-methylthio-7H-pyrrolopyrimidine (4a) with 1-bromo-2,3,5-tri-O-benzyl-D-arabinofuranose (7).Omitting the halogenose and carrying out the reaction of 4a or 4b in dichloromethane leads to the methylene-bridged chromophores 6a and 6b, respectively.In contrast to pyrrolopyrimidines with substituents in position 2 and 4 compound 4a is glycosylated at N-7 and N-1.The formation of anomers and isomers is influenced by the phase-transfer catalyst.The N-1glycosylated 10 is sensitive against hydrolysis at the N-glycosylic bond which is not found for the N-7 isomer 8a.Debenzylation of the methylthio nucleosides 8a or 9a is accomplished using boron trichloride.Raney nickel catalyst removes the sulfur yielding the title compound 2b which exhibits strong fluorescence.