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Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose
http://hdl.handle.net/10487/8162
http://hdl.handle.net/10487/8162faf7ed9b-86b2-47ef-8c48-bc1b617684f4
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
佐藤・化学-001.pdf (4.8 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2011-01-28 | |||||
| タイトル | ||||||
| タイトル | Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
吉村, 寿次
× 吉村, 寿次× Yoshimura, Juji× Kobayashi, Kazuhiko× 佐藤, 憲一× Sato, Ken-ichi× 舟橋, 弥益男× Funabashi, Masuo |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | In order to obtain a 3-C-hydroxymethyl-D-glucose derivative some nucleophilic reactions of 1,2 : 5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (1) and the configurations of products have been examined. Gluco-and allo-configurations of known 3-C-nitromethyl derivatives of 1 were confirmed by the fact that 3-C-acetaminomethyl-1,2-O-isopropylidene-α-D-xylo- and ribo-pentodialdofuranoses, derived by four successive transformations, showed the absence and presence of the aminal-ring formation between the aldehyde and acetamino groups, respectively. A 3-C-carbethoxymethyl derivative obtained by the Reformatsky reaction of 1 with ethyl bromoacetate was proved to be of allo-configuration by the lactone-formation between C5-hydroxyl and carboxyl groups. The configuration of 3-C-hydroxymethyl derivative (15) obtained by treatment of known 3-C-methylene derivative of 1 with permanganate was proved to be of gluco-typc by comparison of the corresponding 3-C-aminomethyl derivative (5), derived by three-step conversions, with that obtained from 3-C-nitromethyl derivatives. 15 was also obtained by epoxidation of 1 with diazomethane followed by ring-opening with alkali. Treatment of 5 and its allo-epimer with nitrous acid gave, respectively, a ring-expanded product and the 3′,5-anhydride, the former being also recognized in the epoxidation products. Structures of new compounds were examined by NMR spectra and stereoselectivity of reactions discussed. | |||||
| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 45, 号 6, p. 1806-1812, 発行日 1972-06 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0009-2673 | |||||
| 書誌レコードID | ||||||
| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA00580132 | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1246/bcsj.45.1806 | |||||
| 著者版フラグ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
| 出版者 | ||||||
| 出版者 | 日本化学会 | |||||
| 資源タイプ | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | Article | |||||
