(2S,3S,4aR,9aR)-3-[(S)-hydroxy(phenyl)methyl]-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-2,4,9,9a-tetrahydroxanthene-2,3-diol | 1263362-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S,3S,4aR,9aR)-3-[(S)-hydroxy(phenyl)methyl]-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-2,4,9,9a-tetrahydroxanthene-2,3-diol
• CAS: 1263362-14-6
• 化学式: C₂₇H₃₆O₇
• 分子量: 472.579
• InChiKey: MFULBMRVEXYIHA-WCCXZMJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4aR,9aR)-3-[(S)-hydroxy(phenyl)methyl]-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-2,4,9,9a-tetrahydroxanthene-2,3-diol 在 sodium tetrahydroborate 、 sodium periodate 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 (6R,7S,8aR,10aR)-6,7-dihydroxy-4-(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102
• 作为产物：
  描述：

  (2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol 在 sodium tetrahydroborate 、 四氧化锇 、 四丙基高钌酸铵 、 cerium(III) chloride heptahydrate 、 水 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 47.42h， 生成 (2S,3S,4aR,9aR)-3-[(S)-hydroxy(phenyl)methyl]-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-2,4,9,9a-tetrahydroxanthene-2,3-diol
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102