((2R,5S)-5-{(1S,4S)-1,4-dihydroxy-4-[(2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl]butyl}tetrahydrofuran-2-yl)methanol | 915314-39-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ((2R,5S)-5-{(1S,4S)-1,4-dihydroxy-4-[(2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl]butyl}tetrahydrofuran-2-yl)methanol
• 英文别名: (1S,4S)-1-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-4-[(2S,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butane-1,4-diol
• CAS: 915314-39-5
• 化学式: C₂₄H₄₆O₆
• 分子量: 430.626
• InChiKey: WSQRLONFEVFEMH-HYLAMMOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((2R,5S)-5-{(1S,4S)-1,4-dihydroxy-4-[(2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl]butyl}tetrahydrofuran-2-yl)methanol 在 2,6-二甲基吡啶 、 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 31.33h， 生成 [(1S)-1-[(2R,5S)-5-[(1S,4S)-1,4-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S,5R)-5-ethenyloxolan-2-yl]butyl]oxolan-2-yl]undecoxy]-tert-butyl-dimethylsilane
  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：

  (5S,6S,9S,10S)-tetradeca-1,12-diene-5,6,9,10-tetraol 在 potassium osmate(VI) 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 sodium periodate 、 十二/十四烷基二甲基氧化胺 、 甲基磺酰胺 、 camphor-10-sulfonic acid 、 silica gel 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 肉桂酸 、 三氟乙酸 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 129.33h， 生成 ((2R,5S)-5-{(1S,4S)-1,4-dihydroxy-4-[(2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl]butyl}tetrahydrofuran-2-yl)methanol
  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.