title: Trimethylsilyl trifluoromethanesulfonate-promoted reductive 2'-O-arylmethylation of ribonucleoside derivatives.
abstract: Arylmethyl groups such as benzyl, p-methoxybenzyl, and 1-pyrenylmethyl groups were introduced to the 2'-O-position of nucleosides by reductive etherification. Combining corresponding aromatic aldehydes with 2'-O-trimethylsilylnucleoside derivatives in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) resulted in moderate to good yields of the 2'-O-arylmethyluridine derivatives, whereas the corresponding cytidine and adenosine derivatives were obtained in low yields. The reaction of ribonucleosides with aliphatic aldehydes did not proceed smoothly. Anomerization of the uridine derivatives by TMSOTf was observed in CH(2)Cl(2), toluene, and CH(3)CN, but was completely suppressed when the reactions were conducted in 1,4-dioxane.
authors.affiliation: Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Chiba, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Uchiyama
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Ogata
authors.forename: Natsuhisa
authors.initials: N
authors.lastname: Oka
authors.forename: Takeshi
authors.initials: T
authors.lastname: Wada
mesh_terms: D008698:Mesylates / Q000737:chemistry*; D008745:Methylation; D010084:Oxidation-Reduction; D012263:Ribonucleosides / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D008698:Mesylates; D012263:Ribonucleosides; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate