(3S,7R,9S)-1-[(benzyloxy)methoxy]-9-(tert-butyldimethylsiloxy)-3-(methoxymethoxy)-3-methyl-5-decyn-7-ol | 1026224-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,7R,9S)-1-[(benzyloxy)methoxy]-9-(tert-butyldimethylsiloxy)-3-(methoxymethoxy)-3-methyl-5-decyn-7-ol
• 英文别名: (2S,4R,8S)-2-[tert-butyl(dimethyl)silyl]oxy-8-(methoxymethoxy)-8-methyl-10-(phenylmethoxymethoxy)dec-5-yn-4-ol
• CAS: 1026224-88-3
• 化学式: C₂₇H₄₆O₆Si
• 分子量: 494.744
• InChiKey: XOTZDJKUWOAYTC-RMDSEJHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,7R,9S)-1-[(benzyloxy)methoxy]-9-(tert-butyldimethylsiloxy)-3-(methoxymethoxy)-3-methyl-5-decyn-7-ol 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 (3S,7R,9S)-1-[(benzyloxy)methoxy]-7,9-O-isopropylidene-3-(methoxymethoxy)-3-methyl-5-decyne-7,9-diol
  参考文献：
  名称：

  Taurospongin A, a Novel Acetylenic Fatty Acid Derivative Inhibiting DNA Polymerase β and HIV Reverse Transcriptase from Sponge Hippospongia sp.

  摘要：

  Taurospongin A (1), a novel acetylene-containing natural product consisting of a taurine and two fatty acid residues, has been isolated from the Okinawan marine sponge Hippospongia sp. and its structure elucidated by spectral data and chemical means. Taurospongin A (1) exhibited potent inhibitory activity against DNA polymerase beta and HIV reverse transcriptase. The absolute configurations of taurospongin A (1) were established to be 3R, 7S, and 9R by synthesis of the MTPA ester of a degradation product of 1.

  DOI：

  10.1021/jo970206r
• 作为产物：
  描述：

  D-甲瓦龙酸?酯 在 4-二甲氨基吡啶 、 正丁基锂 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 52.5h， 生成 (3S,7R,9S)-1-[(benzyloxy)methoxy]-9-(tert-butyldimethylsiloxy)-3-(methoxymethoxy)-3-methyl-5-decyn-7-ol
  参考文献：
  名称：

  Taurospongin A, a Novel Acetylenic Fatty Acid Derivative Inhibiting DNA Polymerase β and HIV Reverse Transcriptase from Sponge Hippospongia sp.

  摘要：

  Taurospongin A (1), a novel acetylene-containing natural product consisting of a taurine and two fatty acid residues, has been isolated from the Okinawan marine sponge Hippospongia sp. and its structure elucidated by spectral data and chemical means. Taurospongin A (1) exhibited potent inhibitory activity against DNA polymerase beta and HIV reverse transcriptase. The absolute configurations of taurospongin A (1) were established to be 3R, 7S, and 9R by synthesis of the MTPA ester of a degradation product of 1.

  DOI：

  10.1021/jo970206r

文献信息

• Taurospongin A, a Novel Acetylenic Fatty Acid Derivative Inhibiting DNA Polymerase β and HIV Reverse Transcriptase from Sponge <i>Hippospongia</i> sp.
  作者：Haruaki Ishiyama、Masami Ishibashi、Akio Ogawa、Shonen Yoshida、Jun'ichi Kobayashi

  DOI：10.1021/jo970206r

  日期：1997.6.13

  Taurospongin A (1), a novel acetylene-containing natural product consisting of a taurine and two fatty acid residues, has been isolated from the Okinawan marine sponge Hippospongia sp. and its structure elucidated by spectral data and chemical means. Taurospongin A (1) exhibited potent inhibitory activity against DNA polymerase beta and HIV reverse transcriptase. The absolute configurations of taurospongin A (1) were established to be 3R, 7S, and 9R by synthesis of the MTPA ester of a degradation product of 1.