(1S,3S,5R)-3-methyl-6,8-dioxabicyclo[3.2.1]octan-3-ol | 1148029-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,3S,5R)-3-methyl-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 1148029-15-5
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: XEOKEWFUFXRHIH-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-丙二硫醇 、 (1S,3S,5R)-3-methyl-6,8-dioxabicyclo[3.2.1]octan-3-ol 在 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(2S,4S)-4-((1,3-dithian-2-yl)methyl)pentane-1,2,4-triol
  参考文献：
  名称：

  Open Chain Chiral Macrolide Building Blocks by Opening of Deoxygenated 1,6-Anhydrosugars with 1,3-Propanedithiol

  摘要：

  Chiral building blocks for macrolides and related natural products are obtained from 1,6-anhydrosugars by conversion of the bicyclic acetals 2 or 12 into the open chain chiral 1,3-dithianes 6 and 13. Branched precursors can be obtained by opening of the Cerny epoxide 1 with the 1,3-dithiane anion to yield 7, followed by ring opening with 1,3-propanedithiol to the bis-1,3-dithiane 8.

  DOI：

  10.1080/07328300802691851
• 作为产物：
  描述：

  甲基氯化镁 、 1,6-anhydro-2,4-dideoxy-β-D-glycero-hexopyranos-3-ulose 在 Glauber's salt 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.33h， 以90%的产率得到(1S,3S,5R)-3-methyl-6,8-dioxabicyclo[3.2.1]octan-3-ol
  参考文献：
  名称：

  Open Chain Chiral Macrolide Building Blocks by Opening of Deoxygenated 1,6-Anhydrosugars with 1,3-Propanedithiol

  摘要：

  Chiral building blocks for macrolides and related natural products are obtained from 1,6-anhydrosugars by conversion of the bicyclic acetals 2 or 12 into the open chain chiral 1,3-dithianes 6 and 13. Branched precursors can be obtained by opening of the Cerny epoxide 1 with the 1,3-dithiane anion to yield 7, followed by ring opening with 1,3-propanedithiol to the bis-1,3-dithiane 8.

  DOI：

  10.1080/07328300802691851

文献信息

• Open Chain Chiral Macrolide Building Blocks by Opening of Deoxygenated 1,6-Anhydrosugars with 1,3-Propanedithiol
  作者：Karsten Krohn、Ishtiaq Ahmed、Dietmar Gehle、Mohammed Al Sahli

  DOI：10.1080/07328300802691851

  日期：2009.2.27

  Chiral building blocks for macrolides and related natural products are obtained from 1,6-anhydrosugars by conversion of the bicyclic acetals 2 or 12 into the open chain chiral 1,3-dithianes 6 and 13. Branched precursors can be obtained by opening of the Cerny epoxide 1 with the 1,3-dithiane anion to yield 7, followed by ring opening with 1,3-propanedithiol to the bis-1,3-dithiane 8.