3,5-di-O-benzyl-2-deoxy-α-D-ribofuranosyl azide | 1200119-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-benzyl-2-deoxy-α-D-ribofuranosyl azide
• 英文别名: (2R,3S,5S)-5-azido-3-phenylmethoxy-2-(phenylmethoxymethyl)oxolane
• CAS: 1200119-13-6
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: DHTQAJXGHRACPV-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-O-Acetyl-3,5-di-O-benzyl-2-desoxy-D-ribofuranose 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl azide 、 3,5-di-O-benzyl-2-deoxy-α-D-ribofuranosyl azide
  参考文献：
  名称：

  Stereoselective Construction of 1β-Azide- and 1β-Cyano-2-deoxyribose Derivatives

  摘要：

  A new method has been developed for the beta-selective introduction of azido and cyano groups at the anomeric position of 2-deoxyribose derivatives. This method proceeds via the formation of a collidinium salt intermediate and allows for the stereoselective construction of 1 beta-azido- and 1 beta-cyano-2-deoxy-D-ribose derivatives. 2-Deoxy-D-ribose compounds bearing an acetoxy or tert-butoxycarbonyloxy group at their anomeric position performed well as starting materials for the formation of the corresponding 1 beta-azide and 1 beta-cyanide derivatives, respectively. H-1 NMR studies of the salt intermediates revealed that the nucleophilic substitution reaction of the salt intermediates proceeded in a S(N)2-fashion.

  DOI：

  10.3987/com-14-s(k)86

文献信息

• Highly diastereoselective allylation of lactols and their ethers using molecular iodine
  作者：J.S. Yadav、B.V. Subba Reddy、A. Srinivas Reddy、Ch. Suresh Reddy、S. Satyanarayana Raju

  DOI：10.1016/j.tetlet.2009.09.025

  日期：2009.12

  Lactols and their ethers undergo smooth allylation with allyltrimethylsilane in the presence of 5 mol % iodine in dichloromethane at −78 °C to afford C-allylfuranosides in good yields and with high diastereoselectivity. The use of iodine makes this method simple, convenient and practical. This is the first report on the allylation of lactols with allyltrimethylsilane using molecular iodine as a catalyst

  在二氯甲烷中，在-78°C下，在5 mol％碘的存在下，乳糖醇及其醚与烯丙基三甲基硅烷进行平滑烯丙基化反应，从而以高收率和高非对映选择性提供C-烯丙基呋喃糖苷。碘的使用使该方法简单，方便和实用。这是关于使用分子碘作为催化剂，将内酯与烯丙基三甲基硅烷进行烯丙基化的首次报道。增强的非对映选择性是该协议的关键功能。
• Stereoselective Construction of 1β-Azide- and 1β-Cyano-2-deoxyribose Derivatives
  作者：Hiromichi Fujioka、Kazuhisa Okamoto、Yutaka Minamitsuji、Yoshifumi Ueyama、Nao Matsumoto、Kenichi Murai

  DOI：10.3987/com-14-s(k)86

  日期：——

  A new method has been developed for the beta-selective introduction of azido and cyano groups at the anomeric position of 2-deoxyribose derivatives. This method proceeds via the formation of a collidinium salt intermediate and allows for the stereoselective construction of 1 beta-azido- and 1 beta-cyano-2-deoxy-D-ribose derivatives. 2-Deoxy-D-ribose compounds bearing an acetoxy or tert-butoxycarbonyloxy group at their anomeric position performed well as starting materials for the formation of the corresponding 1 beta-azide and 1 beta-cyanide derivatives, respectively. H-1 NMR studies of the salt intermediates revealed that the nucleophilic substitution reaction of the salt intermediates proceeded in a S(N)2-fashion.