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Base catalyzed elimination reactions at the 2\u0027, 3\u0027-positions of purine and pyrimidine nucleosides proved to be regiospecific. In the pyrimidine series, the resulting 2\u0027, 3\u0027-olefins with a leaving group at the C-2\u0027 readily formed the corresponding 3\u0027-deoxy-2\u0027-keto-nucleosides, an entirely new class of bioorganic substances.\u003cbr/\u003eExploratory experiments aiming at base-sugar cyclization at the 4\u0027 -positions of nucleosides led to the N[3],C[4\u0027]-cyclization with concomitant decyclization of the base moiety in adenosine series, while in the pyrimidine series the first synthesis of O[2],C[4\u0027]-Crcyclonucleosides was achieved. Synthetic studies on the hitherto unexploited nitrogen-bridged cyclonucleosides were extensively conducted. 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Chemical modifications of natural nucleosides
https://doi.org/10.18999/memsenu.48.2.91
https://doi.org/10.18999/memsenu.48.2.914e7ae7c8-91fc-4581-b2a7-fa8ac4fe032e
名前 / ファイル | ライセンス | アクション |
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Item type | 紀要論文 / Departmental Bulletin Paper(1) | |||||
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公開日 | 2020-10-23 | |||||
タイトル | ||||||
タイトル | Chemical modifications of natural nucleosides | |||||
言語 | en | |||||
著者 |
Minamoto, Katsumaro
× Minamoto, Katsumaro |
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アクセス権 | ||||||
アクセス権 | open access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
抄録 | ||||||
内容記述 | Some chemical modifications of natural nucleosides based on the general organic chemistry have been carried out. Base catalyzed elimination reactions at the 2', 3'-positions of purine and pyrimidine nucleosides proved to be regiospecific. In the pyrimidine series, the resulting 2', 3'-olefins with a leaving group at the C-2' readily formed the corresponding 3'-deoxy-2'-keto-nucleosides, an entirely new class of bioorganic substances.<br/>Exploratory experiments aiming at base-sugar cyclization at the 4' -positions of nucleosides led to the N[3],C[4']-cyclization with concomitant decyclization of the base moiety in adenosine series, while in the pyrimidine series the first synthesis of O[2],C[4']-Crcyclonucleosides was achieved. Synthetic studies on the hitherto unexploited nitrogen-bridged cyclonucleosides were extensively conducted. The major topics cover (a) general synthesis of 2,3'-imino and (substituted-imino) pyrimidine nucleosides,(b) regio and stereospecific synthesis of some reversed nucleosides through protected pyrimidine 6,5'-N-cyclonucleosides, (c) general synthesis of purine 8,5'-N-cyclonucleosides, (d) synthesis and chemistry of purine 8,2'- and 8,3'-long-bridged cyclonucleosides, (e) hydrolytic cleavage of the nitrogen bridge in the 2,2'- and 2,3'-(substituted-imino) pyrimidine nucleosides,(f) molecular rearrangements through the fission of the glycosidic bond in the general N-bridged cyclonucleosides, (g) strain-assisted hydrolysis of the nitrogen bridge of a pyrimidine multi-cyclic N-cyclonucleoside and (h) synthesis and chemistry of piperidine sugar uracil nucleosides. The final topic presents the synthesis and chemistry of 3-deoxy-3-nitro-hexopyranosyl nucleosides in both pyrimidine and purine series. The major results are stereoselective Michael addition reactions of various nucleophiles to the 3-nitro-2,3-unsaturated sugar nucleosides in both cases. | |||||
言語 | en | |||||
内容記述タイプ | Abstract | |||||
出版者 | ||||||
言語 | en | |||||
出版者 | School of Engineering, Nagoya University | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源 | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | departmental bulletin paper | |||||
出版タイプ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
ID登録 | ||||||
ID登録 | 10.18999/memsenu.48.2.91 | |||||
ID登録タイプ | JaLC | |||||
ISSN(print) | ||||||
収録物識別子タイプ | PISSN | |||||
収録物識別子 | 0919-0805 | |||||
書誌情報 |
en : Memoirs of the School of Engineering, Nagoya University 巻 48, 号 2, p. 91-131, 発行日 1997-03-31 |
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著者版フラグ | ||||||
値 | publisher |