bis((9H-fluoren-9-yl)methyl) ((2S,3S,E)-6-((2S,3S)-3-((tert-butyldiphenylsilyl)oxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-2-methylhex-5-en-3-yl) phosphate | 1240018-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: bis((9H-fluoren-9-yl)methyl) ((2S,3S,E)-6-((2S,3S)-3-((tert-butyldiphenylsilyl)oxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-2-methylhex-5-en-3-yl) phosphate
• 英文别名: [(E,2S,3S)-6-[(2S,3S)-3-[tert-butyl(diphenyl)silyl]oxy-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxy-2-methylhex-5-en-3-yl] bis(9H-fluoren-9-ylmethyl) phosphate
• CAS: 1240018-09-0
• 化学式: C₅₆H₅₇O₈PSi
• 分子量: 917.123
• InChiKey: USWBYIUIIYQSOG-RHHVSENISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.14
• 重原子数：
  66
• 可旋转键数：
  18
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis((9H-fluoren-9-yl)methyl) ((2S,3S,E)-6-((2S,3S)-3-((tert-butyldiphenylsilyl)oxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-2-methylhex-5-en-3-yl) phosphate 、 三乙胺 以 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Total Synthesis and Evaluation of Phostriecin and Key Structural Analogues

  摘要：

  Full details of the total synthesis of phostriecin (2), the assignment of its relative and absolute stereochemistry, and the resultant structural reassignment of the natural product previously represented as sultriecin (1), a phosphate versus sulfate monoester, are detailed Studies with authentic material confirmed that phostriecin, but not sultriecin, is an effective and selective inhibitor of protein phosphatase 2A (PP2A) defining a mechanism of action responsible for its antitumor activity The extension of the studies to the synthesis and evaluation of a series of key synthetic analogues is disclosed that highlights the importance of the natural product phosphate monoester (vs sulfate or free alcohol, both inactive and > 250-fold), the alpha,beta-unsaturated lactone (12-fold), and the hydrophobic Z,Z,E-triene tail (C12-C22, ca 200-fold) including the unique importance of its unsaturation (50-fold, and no longer PP2A selective)

  DOI：

  10.1021/jo1010203
• 作为产物：
  描述：

  bis((9H-fluoren-9-yl)methyl) ((2S,3S,E)-6-((2S,3S)-3-((tert-butyldiphenylsilyl)oxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-((4-methoxybenzyl)oxy)-2-methylhex-5-en-3-yl) phosphate 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以70%的产率得到bis((9H-fluoren-9-yl)methyl) ((2S,3S,E)-6-((2S,3S)-3-((tert-butyldiphenylsilyl)oxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-2-methylhex-5-en-3-yl) phosphate
  参考文献：
  名称：

  Total Synthesis and Evaluation of Phostriecin and Key Structural Analogues

  摘要：

  Full details of the total synthesis of phostriecin (2), the assignment of its relative and absolute stereochemistry, and the resultant structural reassignment of the natural product previously represented as sultriecin (1), a phosphate versus sulfate monoester, are detailed Studies with authentic material confirmed that phostriecin, but not sultriecin, is an effective and selective inhibitor of protein phosphatase 2A (PP2A) defining a mechanism of action responsible for its antitumor activity The extension of the studies to the synthesis and evaluation of a series of key synthetic analogues is disclosed that highlights the importance of the natural product phosphate monoester (vs sulfate or free alcohol, both inactive and > 250-fold), the alpha,beta-unsaturated lactone (12-fold), and the hydrophobic Z,Z,E-triene tail (C12-C22, ca 200-fold) including the unique importance of its unsaturation (50-fold, and no longer PP2A selective)

  DOI：

  10.1021/jo1010203

文献信息

• Total Synthesis and Evaluation of Phostriecin and Key Structural Analogues
  作者：Christopher P. Burke、Mark R. Swingle、Richard E. Honkanen、Dale L. Boger

  DOI：10.1021/jo1010203

  日期：2010.11.19

  Full details of the total synthesis of phostriecin (2), the assignment of its relative and absolute stereochemistry, and the resultant structural reassignment of the natural product previously represented as sultriecin (1), a phosphate versus sulfate monoester, are detailed Studies with authentic material confirmed that phostriecin, but not sultriecin, is an effective and selective inhibitor of protein phosphatase 2A (PP2A) defining a mechanism of action responsible for its antitumor activity The extension of the studies to the synthesis and evaluation of a series of key synthetic analogues is disclosed that highlights the importance of the natural product phosphate monoester (vs sulfate or free alcohol, both inactive and > 250-fold), the alpha,beta-unsaturated lactone (12-fold), and the hydrophobic Z,Z,E-triene tail (C12-C22, ca 200-fold) including the unique importance of its unsaturation (50-fold, and no longer PP2A selective)