1,2-bis[(4S,5S)-5-but-3-en-1-yl-2,2-dimethyl-1,3-dioxolan-4-yl]ethane | 915314-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis[(4S,5S)-5-but-3-en-1-yl-2,2-dimethyl-1,3-dioxolan-4-yl]ethane
• 英文别名: 1,2-bis((4S,5S)-5-(but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane；(4S,5S)-4-but-3-enyl-5-[2-[(4S,5S)-5-but-3-enyl-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 915314-33-9
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: JBNQMDQGYBGJKE-XSLAGTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis[(4S,5S)-5-but-3-en-1-yl-2,2-dimethyl-1,3-dioxolan-4-yl]ethane 在 potassium osmate(VI) 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 sodium periodate 、 甲基磺酰胺 、 silica gel 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 49.0h， 生成 1-[(4S,5S)-5-but-3-en-1-yl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4S,5S)-5-(3-oxopropyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.

  DOI：

  10.1021/ja0660148
• 作为产物：
  描述：

  1,5,9,13-Tetradecatetraen 在 potassium osmate(VI) 、 Hydroquinone 1,4-phthalazinediyl diether 甲基磺酰胺 、 camphor-10-sulfonic acid 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 16.0h， 生成 1,2-bis[(4S,5S)-5-but-3-en-1-yl-2,2-dimethyl-1,3-dioxolan-4-yl]ethane
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.

  DOI：

  10.1021/ja0660148

文献信息

• Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-<i>cis</i>-Sylvaticin
  作者：Timothy J. Donohoe、Robert M. Harris、Oliver Williams、Gráinne C. Hargaden、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja9049959

  日期：2009.9.9

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.
• Total Synthesis of (+)-<i>cis</i>-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium
  作者：Timothy J. Donohoe、Robert M. Harris、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja0660148

  日期：2006.10.1

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.