1,5,8-trihydroxy-3-hydroxymethyl-4-methylthio-10-2S,3R,4R,5S,6R-3,4,5-trihydroxy-6-hydroxymethyltetrahydro-2H-pyran-2-ylanthracen-9(10H)-one | 1258381-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5,8-trihydroxy-3-hydroxymethyl-4-methylthio-10-2S,3R,4R,5S,6R-3,4,5-trihydroxy-6-hydroxymethyltetrahydro-2H-pyran-2-ylanthracen-9(10H)-one
• 英文别名: 1,5,8-trihydroxy-3-(hydroxymethyl)-4-methylsulfanyl-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• CAS: 1258381-56-4
• 化学式: C₂₂H₂₄O₁₀S
• 分子量: 480.493
• InChiKey: JQJQRBPSGFJVMD-MJQLSKFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  213
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  5,8-bisbenzyloxy-3-tert-butyldimethylsilyloxymethyl-1-hydroxy-4-methylthio-10-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylanthracen-9(10H)-one 在 三溴化硼 、 盐酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以65%的产率得到1,5,8-trihydroxy-3-hydroxymethyl-4-methylthio-10-2S,3R,4R,5S,6R-3,4,5-trihydroxy-6-hydroxymethyltetrahydro-2H-pyran-2-ylanthracen-9(10H)-one
  参考文献：
  名称：

  Approach Toward the Total Synthesis of 5-Hydroxyaloin A

  摘要：

  The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group.

  DOI：

  10.1021/ol102318k

文献信息

• Approach Toward the Total Synthesis of 5-Hydroxyaloin A
  作者：Kristen J. Procko、Hui Li、Stephen F. Martin

  DOI：10.1021/ol102318k

  日期：2010.12.17

  The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group.