New Nucleoside—Sugar Conjugates: 6-N-Glycosyloxyphosphorylated Adenosine Derivatives as Partial Structures of Agrocin 84

摘要

We report the first successful synthesis of 6-N-[(glucofuranos-1-yloxy)phosphoryl]adenosine as a partial structure of Agrocin 84 via a two-step phosphorylation of 2',3',5'-tri-O-benzoyladenosine with a 2,3,5,6-tetra-O-acetylglucofuranoside 1-O-phosphoramidite derivative that has a 2-(trim-ethylsilyl)ethyl group as the phosphate protecting group. A similar nucleoside—sugar conjugate, 6-N-[(ribofuranos-1-yloxy)phosphoryl]adenosine, was also synthesized. The stabilities of these 6-N-[(glycos-1-yloxy)phosphoryl]adenosine derivatives under acidic, basic, and thermal conditions are described. In particular, we found that the P—O bond of these sugar—nucleoside conjugates was selectively cleaved by treatment with 0.1 M NaOH to give 6-N-phosphoryladenosine, while acidic treatment gave directly adenosine with cleavage of the P—N bond.