5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-ol | 1258381-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-ol
• 英文别名: 2-chloro-5,8-bis(phenylmethoxy)-4-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]naphthalen-1-ol
• CAS: 1258381-47-3
• 化学式: C₅₈H₅₃ClO₈
• 分子量: 913.507
• InChiKey: USBWSYGXURTKAN-GWXQQPQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  67
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilylmethanol 、 5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以72%的产率得到((5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-yloxy)methyl)4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilane
  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：

  氯氢醌 在 N-氯代丁二酰亚胺 、 (2-methylpropyl)lithium 、 sodium hydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 54.75h， 生成 5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-ol
  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.