5,6-二氢-6-(3,4,6,13-四羟基-3-甲基-1,7,9,11-十三碳四烯基)-2H-吡喃-2-酮 | 90730-71-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5,6-二氢-6-(3,4,6,13-四羟基-3-甲基-1,7,9,11-十三碳四烯基)-2H-吡喃-2-酮
• 英文名称: dephosphofostriecin B
• 英文别名: (2R)-2-[(1E,3R,4R,6R,7Z,9Z,11E)-3,4,6,13-tetrahydroxy-3-methyltrideca-1,7,9,11-tetraenyl]-2,3-dihydropyran-6-one
• CAS: 90730-71-5
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: KTHVJFIZRQNFEZ-DSWNLJKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-二氢-6-(3,4,6,13-四羟基-3-甲基-1,7,9,11-十三碳四烯基)-2H-吡喃-2-酮 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (2E,4Z,6Z,8R)-8,10-bis(benzoyloxy)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-decatriene
  参考文献：
  名称：

  Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)

  摘要：

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.

  DOI：

  10.1021/jo962166h
• 作为产物：
  描述：

  triethyl-[(1E,3R)-1-iodohexa-1,5-dien-3-yl]oxysilane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 Grubbs catalyst first generation 、 N-乙基二丙胺 、 2,4,6-三异丙基苯磺酰基肼 、 氢氟酸 、 四丁基氟化铵 、 水 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 烯丙基溴化镁 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 50.08h， 生成 5,6-二氢-6-(3,4,6,13-四羟基-3-甲基-1,7,9,11-十三碳四烯基)-2H-吡喃-2-酮
  参考文献：
  名称：

  Dinuclear Asymmetric Zn Aldol Additions:  Formal Asymmetric Synthesis of Fostriecin

  摘要：

  Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to aldehydes in a short and efficient formal asymmetric synthesis of fostriecin, a potent cyctotoxic natural product. This work highlights not only the power of the aldol methodology but also the utility of the akynyl silane aldol adducts, as it is subsequently utilized in a vinyl silane cross-coupling reaction which affords the target molecule in 14 steps for the longest linear sequence in 8.5% overall yield.

  DOI：

  10.1021/ja042435i

文献信息

• FOSTRIECIN DERIVATIVES AND THE PHARMACEUTICAL USES THEREOF
  申请人：Tang Li

  公开号：US20120065171A1

  公开（公告）日：2012-03-15

  Novel Fostriecin (or FST) derivatives represented by formula (I), the pharmaceutical compositions and preparation methods thereof. The pharmaceutical uses of these compounds, especially the use for the preparation of pharmaceutical compositions for treating tumor, inhibiting cell over growth, or lowering myocardial infarction and the injury to cells.

  Novel Fostriecin（或FST）衍生物由公式（I）表示，其药物组成物和制备方法。这些化合物的药物用途，特别是用于制备治疗肿瘤，抑制细胞过度生长或降低心肌梗死和细胞损伤的药物组合物。
• US8623912B2
  申请人：——

  公开号：US8623912B2

  公开（公告）日：2014-01-07
• Dinuclear Asymmetric Zn Aldol Additions:  Formal Asymmetric Synthesis of Fostriecin
  作者：Barry M. Trost、Mathias U. Frederiksen、Julien P. N. Papillon、Paul E. Harrington、Seunghoon Shin、Brock T. Shireman

  DOI：10.1021/ja042435i

  日期：2005.3.1

  Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to aldehydes in a short and efficient formal asymmetric synthesis of fostriecin, a potent cyctotoxic natural product. This work highlights not only the power of the aldol methodology but also the utility of the akynyl silane aldol adducts, as it is subsequently utilized in a vinyl silane cross-coupling reaction which affords the target molecule in 14 steps for the longest linear sequence in 8.5% overall yield.
• Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)
  作者：Dale L. Boger、Masataka Hikota、Bryan M. Lewis

  DOI：10.1021/jo962166h

  日期：1997.3.1

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.