(3a'R,4'R,7a'R)-4'-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2',2'-dimethyltetrahydrospiro[oxirane-2,6'-[1,3]dioxolo[4,5-c]pyran] | 216864-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3a'R,4'R,7a'R)-4'-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2',2'-dimethyltetrahydrospiro[oxirane-2,6'-[1,3]dioxolo[4,5-c]pyran]
• CAS: 216864-62-9
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: VKRQOWYPYXSMAR-AMSAUXSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.68
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3a'R,4'R,7a'R)-4'-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2',2'-dimethyltetrahydrospiro[oxirane-2,6'-[1,3]dioxolo[4,5-c]pyran] 、 双丙酮半乳糖 在 zinc chloride diethyl ether 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以82%的产率得到6-O-(3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthetic Approach to Kdo Glycosides Via Exo-Glycal Epoxides and Rationalization of the Stereo Chemical Outcome

  摘要：

  The use of epoxides obtained by dimethyldioxirane epoxidation of 2,3-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is described. This method offers a simple and stereoselective access to precursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transition states leading to glycosides formation.

  DOI：

  10.1080/07328309808001899
• 作为产物：
  描述：

  2,6-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (3a'R,4'R,7a'R)-4'-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2',2'-dimethyltetrahydrospiro[oxirane-2,6'-[1,3]dioxolo[4,5-c]pyran]
  参考文献：
  名称：

  Synthetic Approach to Kdo Glycosides Via Exo-Glycal Epoxides and Rationalization of the Stereo Chemical Outcome

  摘要：

  The use of epoxides obtained by dimethyldioxirane epoxidation of 2,3-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is described. This method offers a simple and stereoselective access to precursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transition states leading to glycosides formation.

  DOI：

  10.1080/07328309808001899