1,2-O-cyclohexylidene-5-deoxy-α-D-xylofuranose | 1218926-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-cyclohexylidene-5-deoxy-α-D-xylofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-methylspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-ol
• CAS: 1218926-81-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: FUGNGOITVOWISI-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-O-cyclohexylidene-5-deoxy-α-D-xylofuranose 、 甲基磺酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以63%的产率得到1,2-O-cyclohexylidene-5-deoxy-3-O-methanesulfonyl-α-D-xylofuranose
  参考文献：
  名称：

  From d-xylose to terminal polyols: a simple synthetic route

  摘要：

  A simple and efficient synthetic approach toward different terminal alkyl tetraols and triols, starting from D-xylose, is described. The opening of the oxetane ring in a suitably protected 3,5-anhydro-D-xylose derivative with Grignard reagents leads to D-Xylose-derived 5-deoxy-5-C-alkyl derivatives, which are suitable for reduction to terminal polyols after protecting group hydrolysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.006
• 作为产物：
  描述：

  3,5-anhydro-1,2-O-cyclohexylidene-α-D-xylofuranose 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到1,2-O-cyclohexylidene-5-deoxy-α-D-xylofuranose
  参考文献：
  名称：

  From d-xylose to terminal polyols: a simple synthetic route

  摘要：

  A simple and efficient synthetic approach toward different terminal alkyl tetraols and triols, starting from D-xylose, is described. The opening of the oxetane ring in a suitably protected 3,5-anhydro-D-xylose derivative with Grignard reagents leads to D-Xylose-derived 5-deoxy-5-C-alkyl derivatives, which are suitable for reduction to terminal polyols after protecting group hydrolysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.006

文献信息

• US4515618A
  申请人：——

  公开号：US4515618A

  公开（公告）日：1985-05-07
• From d-xylose to terminal polyols: a simple synthetic route
  作者：Pavle Hadzic、Mirjana Popsavin

  DOI：10.1016/j.carres.2009.12.006

  日期：2010.2

  A simple and efficient synthetic approach toward different terminal alkyl tetraols and triols, starting from D-xylose, is described. The opening of the oxetane ring in a suitably protected 3,5-anhydro-D-xylose derivative with Grignard reagents leads to D-Xylose-derived 5-deoxy-5-C-alkyl derivatives, which are suitable for reduction to terminal polyols after protecting group hydrolysis. (C) 2009 Elsevier Ltd. All rights reserved.