1,5-dideoxy-1,5-imino-D-idurononitrile | 13042-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,5-dideoxy-1,5-imino-D-idurononitrile
• 英文别名: 1-C-cyanoiminoxylitol；2,6-azanediyl-D-2,6-dideoxy-idononitrile；(2R)-3c,4t,5c-trihydroxy-piperidine-2r-carbonitrile；2,6-Didesoxy-2,6-imino-D-idon(gulon)-saeurenitril；2-Amino-2,6-anhydro-2-desoxy-D-idonsaeurenitril；2,6-Anhydro-2-desoxy-idonsaeurenitril；(2R,3S,4S,5R)-3,4,5-trihydroxypiperidine-2-carbonitrile
• CAS: 13042-57-4
• 化学式: C₆H₁₀N₂O₃
• 分子量: 158.157
• InChiKey: KOTKTRIZKDUYEA-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  96.5
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-dideoxy-1,5-imino-D-idurononitrile 在 platinum(IV) oxide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 20.0h， 生成 1-N-(dansyl)amino-1,2,6-dideoxy-2,6-imino-D-iditol
  参考文献：
  名称：

  Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

  摘要：

  A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.03.069
• 作为产物：
  描述：

  sodium cyanide 、 5-azido-5-deoxy-α,β-D-xylose 在 三甲基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.5h， 以98%的产率得到1,5-dideoxy-1,5-imino-D-idurononitrile
  参考文献：
  名称：

  Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

  摘要：

  A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.03.069

文献信息

• Paulsen,H.; Maeckel,E., Chemische Berichte, 1969, vol. 102, p. 3844 - 3853
  作者：Paulsen,H.、Maeckel,E.

  DOI：——

  日期：——
• Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy
  作者：Manuel Zoidl、Bernhard Müller、Ana Torvisco、Christina Tysoe、Mohamed Benazza、Aloysius Siriwardena、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.bmcl.2014.03.069

  日期：2014.6

  A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.