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 | 915314-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 915314-59-9
• 化学式: C₁₉H₃₂O₅
• 分子量: 340.46
• InChiKey: GSNBFXIHZIWUHZ-QAETUUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  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 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 potassium osmate(VI) 2,6-二甲基吡啶 、 四丙基高钌酸铵 、 十二/十四烷基二甲基氧化胺 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 、 肉桂酸 、 乙酰氯 、 对甲苯磺酰肼 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 116.66h， 生成 4,36-epi,epi-cis-sylvaticin
  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-[(4S,5S)-5-but-3-en-1-yl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4S,5S)-5-(3,4-dihydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到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

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.