(4aR,8R,8aS)-8-hydroxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine-6-carbaldehyde | 1051367-45-3

• 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: (4aR,8R,8aS)-8-hydroxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine-6-carbaldehyde
• CAS: 1051367-45-3
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: CCQZAKHJKSHUDW-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-7-(methylsulfinylmethyl)-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane 在 吡啶 、 三氟乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以44%的产率得到(4aR,8R,8aS)-8-hydroxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine-6-carbaldehyde
  参考文献：
  名称：

  Thermodynamics versus kinetics in hetero-Michael cyclizations: a highly stereoselective approach to access both epimers of a C-d-mannopyranoside

  摘要：

  A simple method for the stereocontrolled synthesis of both alpha and beta pseudo-anomers of a thio-functionalized C-glycoside is described. A 2,3:4,6-di-O-isopropylidene manno scaffold is employed to allow a strict control of the diastereoselectivity of the base-catalyzed intramolecular hetero-Michael addition of an alcohol to a vinyl sulfone, by simply changing the temperature of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.117

文献信息

• Thermodynamics versus kinetics in hetero-Michael cyclizations: a highly stereoselective approach to access both epimers of a C-d-mannopyranoside
  作者：Vincent Aucagne、Arnaud Tatibouët、Patrick Rollin

  DOI：10.1016/j.tetlet.2008.05.117

  日期：2008.8

  A simple method for the stereocontrolled synthesis of both alpha and beta pseudo-anomers of a thio-functionalized C-glycoside is described. A 2,3:4,6-di-O-isopropylidene manno scaffold is employed to allow a strict control of the diastereoselectivity of the base-catalyzed intramolecular hetero-Michael addition of an alcohol to a vinyl sulfone, by simply changing the temperature of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.