(+)-cis-sylvaticin | 168039-22-3

• 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: (+)-cis-sylvaticin
• 英文别名: (2S)-4-[(2R)-9-[(2S,5S)-5-[(1S,4S)-1,4-dihydroxy-4-[(2S,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxynonyl]-2-methyl-2H-furan-5-one
• CAS: 168039-22-3
• 化学式: C₃₇H₆₆O₈
• 分子量: 638.926
• InChiKey: HKMBLJVHVBJAIH-PDXBLBMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  45
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+)-cis-sylvaticin 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Shi, Guoen; Zeng, Lu; Gu, Zhe-ming, Heterocycles, 1995, vol. 41, # 8, p. 1785 - 1796

  摘要：

  DOI：
• 作为产物：
  描述：

  在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到(+)-cis-sylvaticin
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  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.

  DOI：

  10.1021/ja9049959

文献信息

• Total Synthesis of <i>cis</i>-Sylvaticin
  作者：Lynda J. Brown、Ian B. Spurr、Stephen C. Kemp、Nicholas P. Camp、Karl R. Gibson、Richard C. D. Brown

  DOI：10.1021/ol800767e

  日期：2008.6.1

  An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP 4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.

  描述了（+）-顺式-sylvaticin的不对称全合成。关键步骤包括使用高锰酸盐介导的1,5-二烯的氧化环化反应合成两个主要片段2和3，以及使用催化有效的束缚RCM结合这些含THF的片段。另外，发现t-BuP 4碱能可靠地促进丁烯内酯前体片段4的快速烷基化。
• 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.
• 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.
• Shi, Guoen; Zeng, Lu; Gu, Zhe-ming, Heterocycles, 1995, vol. 41, # 8, p. 1785 - 1796
  作者：Shi, Guoen、Zeng, Lu、Gu, Zhe-ming、McDougal, John M.、McLaughlin, Jerry L.

  DOI：——

  日期：——