Nucleosides and nucleotides. 191 : Ring expansion reaction of 1-[2,3,5-tri-o-TBS-4α-formyl-β-D-ribo-pentofuranosyl]uracil by treating with (methylene)triphenylphosphorane to give a new nucleoside containing dihydrooxepine ring at the sugar moiety |
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Authors: | Makoto Nomura Kanji Endo Satoshi Shuto Akira Matsuda |
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Institution: | a Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan;b Hanno Research Center, Taiho Pharmaceutical Co. Ltd., 1-27 Misugidai, Hanno, Saitama 357-8527, Japan |
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Abstract: | When 1-2,3,5-tri-O-TBS-4α-formyl-β-D-ribo-pentofuranosyl]uracil (5) was treated with (methylene)triphenylphosphorane in THF, an unusual ring-expansion reaction occurred to give a nucleoside (7) containing dihydrooxepine ring at the sugar moiety. A deuterium-label experiment showed that one carbon unit derived from the ylide was incorporated into the 5'-position of 7. A ring cleavage between the C-3' and C-4' of 5 during the reaction was suggested. |
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Keywords: | Nucleosides Dihydrooxepine Ring-expansion Wittig reactions |
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