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Branched-chain Sugars. IX. Reaction of 3,6-Anhydro-1,2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose with Nitromethane or Hydrogen Cyanide
http://hdl.handle.net/10487/8167
http://hdl.handle.net/10487/8167d221c71e-2cc0-4ca7-b6e2-f4f1f8fc12e3
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
佐藤・化学-006.pdf (3.5 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. IX. Reaction of 3,6-Anhydro-1,2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose with Nitromethane or Hydrogen Cyanide | |||||
| 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 |
佐藤, 憲一
× 佐藤, 憲一× Sato, Ken-ichi× 吉村, 寿次× Yoshimura, Juji× 辛, 重基× Shin, Chung-gi |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | 3,6-Anhydro-1,2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (2) was converted into 5,6-di-O-acetyl-1, 2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (5) by the protection of the carbonyl function with hydroxylamine, followed by acetylation and removal of the protecting group with chromium(II) acetate. Nitromethane condensation of 2 and 5 at room temperature gave the corresponding 3-nitromethyl derivatives having D-gluco- and D-allo-configuration, respectively. The difference in the stereoselectivity was explained by the easiness of isomerization of the initial product to thermodynamically stable epimer, because the reaction temperature was essential to control the selectivity in the same reaction of 1,2 : 5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose. Reaction of 2 with hydrogen cyanide in dry pyridine followed by acetylation gave the corresponding 3,5,6-tri-O-acetyl-3-cyano derivative of D-allo-type, whereas, the reaction in water gave instantly 3-(hydroxycarbonimidoyl)-1,2-O-isopropylidene-α-D-allofuranose 3′,5-lactone, by the participation of the C5-hydroxyl group. | |||||
| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 50, 号 5, p. 1191-1194, 発行日 1977-05 |
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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.50.1191 | |||||
| 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 | |||||
