87791-29-5Relevant academic research and scientific papers
ara-7-Deazanebularine - Synthesis of a Fluorescent Pyrrolopyrimidine Nucleoside by Phase-Transfer Glycosylation
Seela, Frank,Steker, Herbert
, p. 1576 - 1587 (2007/10/02)
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.
