1,5:3,6-dianhydro-D-galactitol | 98969-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 1,5:3,6-dianhydro-D-galactitol
• 英文别名: D-1,5;3,6-dianhydro-galactitol；D-1,5;3,6-Dianhydro-galactit；(1R,4S,5R,8S)-2,6-dioxabicyclo[3.2.1]octane-4,8-diol
• CAS: 98969-11-0
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: YOSORPVRDQOTPQ-BGPJRJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,5:3,6-dianhydro-D-galactitol 以 吡啶 为溶剂， 反应 12.0h， 生成 [(1R,4S,5R,8S)-8-acetyloxy-2,6-dioxabicyclo[3.2.1]octan-4-yl] acetate
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p
• 作为产物：
  描述：

  [(1R,4S,5R,8S)-8-acetyloxy-2,6-dioxabicyclo[3.2.1]octan-4-yl] acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以248 mg的产率得到1,5:3,6-dianhydro-D-galactitol
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p

文献信息

• Borane- and Silylium-Catalyzed Difunctionalization of Carbohydrates: 3,6-Anhydrosugar Enabled 1,6-Site Selectivity
  作者：Joshua J. Clarke、Kevin Basemann、Neyen Romano、Stephen J. Lee、Michel R. Gagné

  DOI：10.1021/acs.orglett.2c01243

  日期：2022.6.17

  A novel diastereoselective, Lewis acid catalyzed 1,6-difunctionalization of galactose and mannose derivatives has been developed in one pot, via sequential nucleophile additions. Our studies point to the formation of a 3,6-anhydrosugar intermediate as key to the 1,6-site-selectivity. Starting material-specific reactivity occurs when competitive ring-opening C–O cleavage is possible, owed to basicity

  一种新型的非对映选择性路易斯酸催化的半乳糖和甘露糖衍生物的 1,6-双官能化已经通过连续的亲核试剂加成在一个锅中开发出来。我们的研究指出 3,6-脱水糖中间体的形成是 1,6 位点选择性的关键。由于碱度和立体电子稳定性的差异，当竞争性开环 C-O 裂解成为可能时，就会发生起始材料特异性反应。最后，Mayr 亲核性参数值有助于预测哪些反应条件最适合特定的亲核试剂。
• The Synthesis of 1,5:3,6-Dianhydro-D-galactitol (D-Neogalactide)
  作者：Hewitt G. Fletcher、C. S. Hudson

  DOI：10.1021/ja01158a063

  日期：1950.2
• Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis
  作者：Justin B. Houseknecht、Todd L. Lowary

  DOI：10.1021/jo011127p

  日期：2002.6.1

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.