((3aR)-7c-Methoxy-2,2-dimethyl-(3ar,7at)-3a,4,7,7a-tetrahydro-6H-spirodioxole-5,2'-<1,3>dithian>-4t-yl)methanol | 160708-47-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: ((3aR)-7c-Methoxy-2,2-dimethyl-(3ar,7at)-3a,4,7,7a-tetrahydro-6H-spirodioxole-5,2'-<1,3>dithian>-4t-yl)methanol
• 英文别名: [(3aR)-7c-Methoxy-2,2-dimethyl-(3ar,7at)-3a,4,7,7a-tetrahydro-6H-spiro[benzo[1,3]dioxole-5,2'-[1,3]dithian]-4t-yl]methanol；[(3'aR,4'S,7'S,7'aR)-7'-methoxy-2',2'-dimethylspiro[1,3-dithiane-2,5'-4,6,7,7a-tetrahydro-3aH-1,3-benzodioxole]-4'-yl]methanol
• CAS: 160708-47-4
• 化学式: C₁₄H₂₄O₄S₂
• 分子量: 320.474
• InChiKey: HEVVYMPEVKNIDL-NNYUYHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3aR)-7c-Methoxy-2,2-dimethyl-(3ar,7at)-3a,4,7,7a-tetrahydro-6H-spirodioxole-5,2'-<1,3>dithian>-4t-yl)methanol 在 Raney nickel W-2 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 5a-carba-1,5-anhydro-L-iditol
  参考文献：
  名称：

  From Sugars to Carbocycles. 3. Synthesis of Validatol and 4-epi-Validatol from Mannose and Glucose

  摘要：

  Validatol (4) and 4-epi-validatol (8) are synthesized from mannose and glucose, respectively. The key step in the synthesis of 4 is the base-induced intramolecular displacement reaction of the epoxy dithiane 14 to yield the six-membered carbocycle 15 exclusively.

  DOI：

  10.1021/jo00099a044
• 作为产物：
  描述：

  6,7-Anhydro-2-deoxy-4,5-O-isopropylidene-3-O-methyl-D-gluco-heptose trimethylene dithioacetal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以70%的产率得到((3aR)-7c-Methoxy-2,2-dimethyl-(3ar,7at)-3a,4,7,7a-tetrahydro-6H-spirodioxole-5,2'-<1,3>dithian>-4t-yl)methanol
  参考文献：
  名称：

  From Sugars to Carbocycles. 3. Synthesis of Validatol and 4-epi-Validatol from Mannose and Glucose

  摘要：

  Validatol (4) and 4-epi-validatol (8) are synthesized from mannose and glucose, respectively. The key step in the synthesis of 4 is the base-induced intramolecular displacement reaction of the epoxy dithiane 14 to yield the six-membered carbocycle 15 exclusively.

  DOI：

  10.1021/jo00099a044

文献信息

• From Sugars to Carbocycles. 3. Synthesis of Validatol and 4-epi-Validatol from Mannose and Glucose
  作者：Karsten Krohn、Guido Boerner、Stephan Gringard

  DOI：10.1021/jo00099a044

  日期：1994.10

  Validatol (4) and 4-epi-validatol (8) are synthesized from mannose and glucose, respectively. The key step in the synthesis of 4 is the base-induced intramolecular displacement reaction of the epoxy dithiane 14 to yield the six-membered carbocycle 15 exclusively.