tert-butyldimethyl(((4S,5S,6S,7Z,9Z,11E)-5-methyl-4-(sulfoxy)heptadeca-1,7,9,11-tetraen-6-yl)oxy)silane | 1240017-98-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: tert-butyldimethyl(((4S,5S,6S,7Z,9Z,11E)-5-methyl-4-(sulfoxy)heptadeca-1,7,9,11-tetraen-6-yl)oxy)silane
• 英文别名: [(4S,5S,6S,7Z,9Z,11E)-6-[tert-butyl(dimethyl)silyl]oxy-5-methylheptadeca-1,7,9,11-tetraen-4-yl] hydrogen sulfate
• CAS: 1240017-98-4
• 化学式: C₂₄H₄₄O₅SSi
• 分子量: 472.762
• InChiKey: ZRXSCUVBQSEKSA-PKPTWNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4S,5R,6S,7Z,9Z,11E)-6-((tert-butyldimethylsilyl)oxy)-5-methylheptadeca-1,7,9,11-tetraen-4-ol 在 三氧化硫吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以98%的产率得到tert-butyldimethyl(((4S,5S,6S,7Z,9Z,11E)-5-methyl-4-(sulfoxy)heptadeca-1,7,9,11-tetraen-6-yl)oxy)silane
  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)