(1S*,4R*,1'S*)-1-O-tert-butyldimethylsilyl-4-(1'-hydroxyethyl)-4,1'-O-isopropylidene-2-cyclopentene-1,4-diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S*,4R*,1'S*)-1-O-tert-butyldimethylsilyl-4-(1'-hydroxyethyl)-4,1'-O-isopropylidene-2-cyclopentene-1,4-diol
• 英文别名: tert-butyl-dimethyl-[[(4R,5S,7R)-2,2,4-trimethyl-1,3-dioxaspiro[4.4]non-8-en-7-yl]oxy]silane
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: JLQYYBTVOCUVOM-DVOMOZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone 在 正丁基锂 、 水 、 4-甲基苯磺酸吡啶 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 (1S*,4R*,1'S*)-1-O-tert-butyldimethylsilyl-4-(1'-hydroxyethyl)-4,1'-O-isopropylidene-2-cyclopentene-1,4-diol
  参考文献：
  名称：

  First total syntheses and configurational assignments of cytotoxic trichodenones A–C

  摘要：

  Total syntheses of cytotoxic trichodenones A-C, produced by a strain of Trichoderma harzianum from the sponge Halichondria okadai, have been achieved, and the natural trichodenones B and C have been established to have (4R,1'R)- and(1'R)-configurations, respectively. From this synthesis and chiral HPLC analysis, it was deduced that the major molecule with R-configuration coexists with its enantiomer in natural trichodenone A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00329-3

文献信息

• First total syntheses and configurational assignments of cytotoxic trichodenones A–C
  作者：Yoshihide Usami、Takashi Ikura、Taro Amagata、Atsushi Numata

  DOI：10.1016/s0957-4166(00)00329-3

  日期：2000.9

  Total syntheses of cytotoxic trichodenones A-C, produced by a strain of Trichoderma harzianum from the sponge Halichondria okadai, have been achieved, and the natural trichodenones B and C have been established to have (4R,1'R)- and(1'R)-configurations, respectively. From this synthesis and chiral HPLC analysis, it was deduced that the major molecule with R-configuration coexists with its enantiomer in natural trichodenone A. (C) 2000 Elsevier Science Ltd. All rights reserved.