[(2R,3R,4aR,5S,7R,8R,8aS)-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-5-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-7-yl]methoxy-tert-butyl-dimethylsilane | 1326704-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4aR,5S,7R,8R,8aS)-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-5-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-7-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1326704-67-9
• 化学式: C₂₈H₄₈O₉Si
• 分子量: 556.769
• InChiKey: PXGIALZTTNOTET-TTWDJJBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4aR,5S,7R,8R,8aS)-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-5-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-7-yl]methoxy-tert-butyl-dimethylsilane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 、
  参考文献：
  名称：

  Carbocyclization of d-glucose: syntheses of gabosine I and streptol

  摘要：

  D-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic intermediate, enone 13, which was readily transformed into gabosine I and streptol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.028
• 作为产物：
  描述：

  (2R,3R,4aR,5S,7R,8R,8aS)-7-(hydroxymethyl)-2,3-dimethoxy-2,3-dimethyl-5-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-8-ol 在 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 [(2R,3R,4aR,5S,7R,8R,8aS)-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-5-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-7-yl]methoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Carbocyclization of d-glucose: syntheses of gabosine I and streptol

  摘要：

  D-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic intermediate, enone 13, which was readily transformed into gabosine I and streptol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.028

文献信息

• Carbocyclization of d-glucose: syntheses of gabosine I and streptol
  作者：Tony K.M. Shing、Y. Chen、Wai-Lung Ng

  DOI：10.1016/j.tet.2011.06.028

  日期：2011.8

  D-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic intermediate, enone 13, which was readily transformed into gabosine I and streptol. (C) 2011 Elsevier Ltd. All rights reserved.