(2S)-4-(4,4-ethylenedioxy-1-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-butyn-2-yl [2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4,6-O-isopropylidene]-β-D-glucopyranoside | 1119768-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-4-(4,4-ethylenedioxy-1-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-butyn-2-yl [2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4,6-O-isopropylidene]-β-D-glucopyranoside
• CAS: 1119768-86-3
• 化学式: C₃₆H₆₂O₁₀Si₂
• 分子量: 711.053
• InChiKey: RWXSRYLIEVPZGJ-FNMBMZSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  48.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S)-4-(4,4-ethylenedioxy-1-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-butyn-2-yl [2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4,6-O-isopropylidene]-β-D-glucopyranoside 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以74%的产率得到(2S,3E)-4-(4,4-ethylenedioxy-1-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-yl [2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4,6-O-isopropylidene]-β-D-glucopyranoside
  参考文献：
  名称：

  A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells

  摘要：

  Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.002
• 作为产物：
  描述：

  7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 、 (2S)-3-butyn-2-yl [2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4,6-O-isopropylidene]-β-D-glucopyranoside 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.33h， 以97%的产率得到(2S)-4-(4,4-ethylenedioxy-1-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-butyn-2-yl [2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4,6-O-isopropylidene]-β-D-glucopyranoside
  参考文献：
  名称：

  A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells

  摘要：

  Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.002