The Synthesis of C-Methyl Branched-Chain Deoxy Sugar Nucleosides by the Deoxygenative Methylation of O-Tosylated Adenosines with Grignard Reagents

Article abstract of DOI:10.1246/bcsj.61.2437

The reaction of appropiately protected 2'-O-tosyladenosines with methylmagnesium bromide (or iodide) gave 9-(2-deoxy-3-C-methyl-β-D-threopentofuranosyl)adenine after deprotection.The same reaction on 3'-O-tosyladenosine derivatives afforded an epimeric pair of 2'-C-methyl-3'-deoxy sugar nucleosides.The modified structures of the sugar moieties were determined unambiguously.