Synthesis of 8,6'-Cyclo-6'-deoxyhexofuranosyladenines : Adenosines Fixed in an Anti-conformation (Nucleosides and Nucleotides. LXVI)

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For studies of the conformation of nucleosides around the glycosyl linkages, the carbonbridged cycloadenosines, 8,6'-cyclo-6'-deoxyallofuranosyladenine and its 5'-epimer, were synthesized by the following route. Treatment of N^6-benzoyl-2', 3'-O-isopropylideneadenosine 5'-aldehyde (1) with dimethyloxosulfonium methylide afforded the 5', 6'-anhydrohexofuranosyladenine (2), which was treated with thiophenoxide to give the diastereomeric 6'-phenylthio derivatives (4). Photoirradiation of 4 followed by 5'-O-acetylation afforded 5'-O-acetyl-8,6'-cyclo-6'-deoxy-hexofuranosyladenine derivatives (6b, 7b). Attempted synthesis of a 8,7'-cyclo-heptofuranosyl derivative by way of photolysis of a 7'-phenylthio-heptofuranosyladenine resulted in the formation of 5', 6', 7'-trideoxy-2', 3'-O-isopropylidene-β-D-ribo-heptofuranosyladenine (11). The nature of the circular dichroism spectra of 6 and 7 is discussed.
公益社団法人日本薬学会の論文
1986-04-25