(1R,3R,5R,6S,7R,9R,11R,12S)-5,11-bis(ethenyl)-6,12-bis(prop-2-enoxy)-2,4,8,10-tetraoxatricyclo[7.3.0.03,7]dodecane | 1394922-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (1R,3R,5R,6S,7R,9R,11R,12S)-5,11-bis(ethenyl)-6,12-bis(prop-2-enoxy)-2,4,8,10-tetraoxatricyclo[7.3.0.03,7]dodecane
• CAS: 1394922-27-0
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: FOZSTLPPKQJBJJ-VMAIWCPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3R,5R,6S,7R,9R,11R,12S)-5,11-bis(ethenyl)-6,12-bis(prop-2-enoxy)-2,4,8,10-tetraoxatricyclo[7.3.0.03,7]dodecane 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以82%的产率得到
  参考文献：
  名称：

  Deoxygenation/dimerization of sugar derivatives with BF3·Et2O–Et3SiH: synthesis of a β-isonucleoside

  摘要：

  Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained as the sole products, while only the dimeric products are isolated if Et3SiH is excluded. One of the deoxygenated products has been transformed into a beta-isonucleoside. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.121
• 作为产物：
  描述：

  3-O-allyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以78%的产率得到(1R,3R,5R,6S,7R,9R,11R,12S)-5,11-bis(ethenyl)-6,12-bis(prop-2-enoxy)-2,4,8,10-tetraoxatricyclo[7.3.0.03,7]dodecane
  参考文献：
  名称：

  Deoxygenation/dimerization of sugar derivatives with BF3·Et2O–Et3SiH: synthesis of a β-isonucleoside

  摘要：

  Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained as the sole products, while only the dimeric products are isolated if Et3SiH is excluded. One of the deoxygenated products has been transformed into a beta-isonucleoside. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.121

文献信息

• Deoxygenation/dimerization of sugar derivatives with BF3·Et2O–Et3SiH: synthesis of a β-isonucleoside
  作者：Subhrangshu Mukherjee、Biswajit G. Roy、Soumendra N. Das、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2012.06.121

  日期：2012.9

  Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained as the sole products, while only the dimeric products are isolated if Et3SiH is excluded. One of the deoxygenated products has been transformed into a beta-isonucleoside. (C) 2012 Elsevier Ltd. All rights reserved.