3-deoxy-2,5-di-O-benzoylthreo-γ-lactone | 145369-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-deoxy-2,5-di-O-benzoylthreo-γ-lactone
• CAS: 145369-04-6
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: SLXULPLDNYYOQS-HOTGVXAUSA-N

物化性质

• 沸点：
  523.6±35.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+)-二氢香芹酮 、 3-deoxy-2,5-di-O-benzoylthreo-γ-lactone 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到[(2S,4S)-4-[(1S,2R,5R)-1-hydroxy-2-methyl-5-prop-1-en-2-ylcyclohexyl]-5-oxooxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  糖类内酯与SmI 2促进的萜烯酮的高度立体选择性偶联

  摘要：

  使内酯3-脱氧碳水化合物与二碘化sa（SmI 2）在THF / HMPA中和萜烯酮（-）-薄荷酮或（+）-二氢香芹酮反应; 连续的还原性脱氧和伴随的羰基加成反应得到具有高非对映选择性（高达99∶1）的C 2支链糖。

  DOI：

  10.1016/s0040-4039(00)60008-4
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-deoxy-2,5-di-O-benzoylthreo-γ-lactone
  参考文献：
  名称：

  Enholm, Eric J.; Jiang, Shujun, Heterocycles, 1992, vol. 34, # 12, p. 2247 - 2252

  摘要：

  DOI：

文献信息

• Branched-chain carbohydrate lactones from a samarium(II) iodide-promoted serial deoxygenation-carbonyl addition reaction
  作者：Eric J. Enholm、Shujun Jiang、Khalil Abboud

  DOI：10.1021/jo00067a045

  日期：1993.7

  A new deoxygenation-carbonyl addition reaction mediated by samarium(II) iodide (SmI2) in THF/HMPA was examined with carbohydrate lactones and several substrates containing an alpha-alkoxy carboxylic ester. In a single reaction, these compounds were deoxygenated and subsequently coupled to several ketones by a carbonyl addition reaction. The first reactions studied simple ester and ketone adducts which were later elaborated to more complex optically active carbohydrate lactones appended to terpene ketones. Simple esters smoothly afforded beta-hydroxy carbonyl products. Fully benzoate-protected 3-deoxycarbohydrate lactones were reacted with simple ketones to produce C2-branched sugars. The attendant carbonyl addition to the least sterically hindered face of the aldonolactone provided the major products. Moderate diastereoselectivities (up to 5:1) were observed in the simple ketone products as determined by difference NOE studies. Finally, the terpene ketones, (-)-menthone or (+)-dihydrocarvone, were coupled to 3-deoxycarbohydrate lactones which gave C2-branched sugars with very high diastereoselectivities (up to 99:1).