4,7-anhydro-6,7-di-O-benzyl-1,2,3,5-tetradeoxy-D-ribo-oct-1-enitol | 1057653-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,7-anhydro-6,7-di-O-benzyl-1,2,3,5-tetradeoxy-D-ribo-oct-1-enitol
• 英文别名: (2R,3S,5S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-5-prop-2-enyloxolane
• CAS: 1057653-80-1
• 化学式: C₂₂H₂₆O₃
• 分子量: 338.447
• InChiKey: IZHXJDMJKJCFEZ-FDFHNCONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,7-anhydro-6,7-di-O-benzyl-1,2,3,5-tetradeoxy-D-ribo-oct-1-enitol 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-D-ribo-octitol
  参考文献：
  名称：

  Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

  摘要：

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.070
• 作为产物：
  描述：

  4,7-anhydro-1,2,3,5-tetradeoxy-D-ribo-oct-1-enitol 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以66%的产率得到4,7-anhydro-6,7-di-O-benzyl-1,2,3,5-tetradeoxy-D-ribo-oct-1-enitol
  参考文献：
  名称：

  Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

  摘要：

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.070

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 synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction
  作者：Angeles Martín、Inés Pérez-Martín、Luis M. Quintanal、Ernesto Suárez

  DOI：10.1016/j.tetlet.2008.06.070

  日期：2008.8

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.