Studies of nucleosides and nucleotides—XLI
1970; Elsevier BV; Volume: 26; Issue: 18 Linguagem: Inglês
10.1016/s0040-4020(01)93068-6
ISSN1464-5416
AutoresMorio Ikehara, Masakatsu Kaneko,
Tópico(s)Advanced biosensing and bioanalysis techniques
Resumo5′-O-Trityl-, 5′-O-benzoyl-, 5′-O-acetyl- and unprotected 8-bromoadenosine were subjected to sulfonylation using sodium hydride and triisopropyl-benzenesulfonyl chloride in N,N-dimethylformamide solution. In each case 2′- and 3′-monosulfonylated compounds were the main products. The ratio of 2′- to 3′-sulfonylated compound increased as the bulkiness of 5′-substituted group increased. Each sulfonylated product was confirmed as to their structure by elemental analysis and UV and IR absorption properties as well as transformation to 8,2′- and 8,3′-S-cyclonucleosides. The present series of reactions affords a convenient and novel method for the synthesis of purine cyclonucleosides.
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