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 | 1258381-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 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
• 英文别名: 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-hydroxy-4-methylsulfanyl-5,8-bis(phenylmethoxy)-10-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-10H-anthracen-9-one
• CAS: 1258381-55-3
• 化学式: C₇₀H₇₄O₁₀SSi
• 分子量: 1135.5
• InChiKey: QNWAAUGUGMULHG-FPLWBAQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.21
• 重原子数：
  82
• 可旋转键数：
  25
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  tert-butyl-[[6,6-dimethyl-2-methylsulfanyl-11,14-bis(phenylmethoxy)-16-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-8,18-dioxa-6-silapentacyclo[7.7.1.12,5.05,17.010,15]octadeca-1(16),3,9(17),10,12,14-hexaen-3-yl]methoxy]-dimethylsilane 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以83%的产率得到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
  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.