3-O-benzyl-4,5-dideoxy-1,2-O-isopropylidene-α-L-glycero-hex-4-en-2-ulopyranose | 132369-48-3

• 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-O-benzyl-4,5-dideoxy-1,2-O-isopropylidene-α-L-glycero-hex-4-en-2-ulopyranose
• 英文别名: (5S,6S)-2,2-dimethyl-6-phenylmethoxy-1,3,10-trioxaspiro[4.5]dec-7-ene
• CAS: 132369-48-3
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: YCYFUOMLLUYSDD-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,5-dideoxy-1,2-O-isopropylidene-α-L-glycero-hex-4-en-2-ulopyranose 在 氢气 、 镍 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以69%的产率得到(2S,3S)-3,6-dihydro-3-hydroxy-2',2'-dimethyl-2H-pyran-2-spiro-4'-(1',3'-dioxolane)
  参考文献：
  名称：

  Structural Probing of Ketone Catalysts for Asymmetric Epoxidation

  摘要：

  A series of chiral ketones derived from carbohydrates were investigated as catalysts for the asymmetric epoxidation. Fructose-derived ketones are found to be efficient catalysts. The studies show that the structural requirements for the ketone catalysts are very stringent and different types of olefins may require ketones with different structural arrangements. The current study allows us to further understand the chiral ketone catalyzed asymmetric epoxidation and provides some insight for the development of new catalysts.

  DOI：

  10.1021/jo9817218
• 作为产物：
  描述：

  1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 在 咪唑 、 碘 、 potassium hydride 、 溶剂黄146 、 三苯基膦 、 锌 作用下， 反应 4.5h， 生成 3-O-benzyl-4,5-dideoxy-1,2-O-isopropylidene-α-L-glycero-hex-4-en-2-ulopyranose
  参考文献：
  名称：

  Structural Probing of Ketone Catalysts for Asymmetric Epoxidation

  摘要：

  A series of chiral ketones derived from carbohydrates were investigated as catalysts for the asymmetric epoxidation. Fructose-derived ketones are found to be efficient catalysts. The studies show that the structural requirements for the ketone catalysts are very stringent and different types of olefins may require ketones with different structural arrangements. The current study allows us to further understand the chiral ketone catalyzed asymmetric epoxidation and provides some insight for the development of new catalysts.

  DOI：

  10.1021/jo9817218

文献信息

• Controlled Garegg Conditions for Selective Iodination on Pyranose Templates
  作者：Ana-Catarina Simao、Sandrina Silva、Amelia P. Rauter、Patrick Rollin、Arnaud Tatibouët

  DOI：10.1002/ejoc.201001325

  日期：2011.4

  Regio- and stereoselective iodinations under controlled Garegg conditions were performed on vicinal diols and contiguous triols located on pyranose templates. P- D -Fructo- or psicopyranose-based diols were selectively iodinated at C-5 or C-4, respectively, to afford the L -sorbo or D -tagato iodohydrins. In contrast, the related triols only underwent selective iodination at C-5. Application of the

  在受控的 Garegg 条件下，对位于吡喃糖模板上的邻二醇和连续三醇进行区域选择性和立体选择性碘化。基于 P-D-果糖或吡喃吡喃糖的二醇分别在 C-5 或 C-4 处选择性碘化，以提供 L-山梨糖或 D-塔格托碘醇。相比之下，相关的三醇仅在 C-5 处进行选择性碘化。将该方法应用于 D-葡糖苷和 D-吡喃半乳糖苷导致分别在 C-3 或 C-4 处选择性碘化，以提供 D-allo 或 D-葡糖碘醇。
• Selective iodination of vicinal cis-diols on ketopyranose templates
  作者：Ana Catarina Simao、Arnaud Tatibouët、Amelia P. Rauter、Patrick Rollin

  DOI：10.1016/j.tetlet.2010.06.107

  日期：2010.9

  A regio- and stereoselective iodination has been performed on vicinal diols located on ketopyranose templates using the controlled-Garegg conditions. 3-O-Benzy1-1,2-O-isopropylidene-beta-D-fructo- or psicopyranoses (1 or 4) were selectively iodinated, respectively, at C-5 or C-4 of the ketoses to afford the L-sorbo or D-sorbo iodohydrins. (C) 2010 Elsevier Ltd. All rights reserved.
• IZQUIERDO, CUBERO I.;LOPEZ-ESPINOSA, M. T. PLAZA, ANAL. QUIM., 86,(1990) N, C. 554-560
  作者：IZQUIERDO, CUBERO I.、LOPEZ-ESPINOSA, M. T. PLAZA

  DOI：——

  日期：——
• Structural Probing of Ketone Catalysts for Asymmetric Epoxidation
  作者：Yong Tu、Zhi-Xian Wang、Michael Frohn、Mingqi He、Hongwu Yu、Yong Tang、Yian Shi

  DOI：10.1021/jo9817218

  日期：1998.11.1

  A series of chiral ketones derived from carbohydrates were investigated as catalysts for the asymmetric epoxidation. Fructose-derived ketones are found to be efficient catalysts. The studies show that the structural requirements for the ketone catalysts are very stringent and different types of olefins may require ketones with different structural arrangements. The current study allows us to further understand the chiral ketone catalyzed asymmetric epoxidation and provides some insight for the development of new catalysts.