(2R,3R,4aR,7R,8R,8aS)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-4a,7,8,8a-tetrahydropyrano[3,4-b][1,4]dioxin-5-one | 1326704-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,3R,4aR,7R,8R,8aS)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-4a,7,8,8a-tetrahydropyrano[3,4-b][1,4]dioxin-5-one
• CAS: 1326704-69-1
• 化学式: C₂₁H₄₀O₉Si
• 分子量: 464.629
• InChiKey: XTFSQNSCDXPDSB-SHTNYLHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aR,7R,8R,8aS)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-4a,7,8,8a-tetrahydropyrano[3,4-b][1,4]dioxin-5-one 在 sodium tetrahydroborate 、 水 、 potassium tri-sec-butyl-borohydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 三氟乙酸酐 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.08h， 生成 (+)-streptol
  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：

  在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到(2R,3R,4aR,7R,8R,8aS)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-(ethoxymethoxy)-2,3-dimethoxy-2,3-dimethyl-4a,7,8,8a-tetrahydropyrano[3,4-b][1,4]dioxin-5-one
  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.