[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[6-(hydroxymethyl)-2,3-dihydro-1,4-dithiin-5-yl]methyl] acetate | 1040186-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[6-(hydroxymethyl)-2,3-dihydro-1,4-dithiin-5-yl]methyl] acetate
• CAS: 1040186-38-6
• 化学式: C₁₃H₂₀O₅S₂
• 分子量: 320.431
• InChiKey: OGMFPASJNFDJBR-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[6-(hydroxymethyl)-2,3-dihydro-1,4-dithiin-5-yl]methyl] acetate 在 吡啶 、 Celite 、 pyridinium chlorochromate 作用下， 反应 8.0h， 以97%的产率得到[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(6-formyl-2,3-dihydro-1,4-dithiin-5-yl)methyl] acetate
  参考文献：
  名称：

  Rapid Access to 1,6-Anhydro-β-l-hexopyranose Derivatives via Domino Reaction: Synthesis of l-Allose and l-Glucose

  摘要：

  An expeditious and efficient synthesis of 1,6-anhydro-beta-L-hexopyranosyl derivatives 3 as valuable building blocks for the preparation Of L-sugars is herein reported. This route relies upon the use of a domino reaction involving five synthetic steps from the 5,6-dihydro-1,4-dithiin 4. As 1,6-anhydro derivatives 3 are obtained, dithioethylene bridge removal and double-bond dihydroxylation give access to protected L-allose and L-glucose in stereoselective fashion and high yields.

  DOI：

  10.1021/jo800775v
• 作为产物：
  描述：

  [(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[6-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydro-1,4-dithiin-5-yl]methyl] acetate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以72%的产率得到[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[6-(hydroxymethyl)-2,3-dihydro-1,4-dithiin-5-yl]methyl] acetate
  参考文献：
  名称：

  Rapid Access to 1,6-Anhydro-β-l-hexopyranose Derivatives via Domino Reaction: Synthesis of l-Allose and l-Glucose

  摘要：

  An expeditious and efficient synthesis of 1,6-anhydro-beta-L-hexopyranosyl derivatives 3 as valuable building blocks for the preparation Of L-sugars is herein reported. This route relies upon the use of a domino reaction involving five synthetic steps from the 5,6-dihydro-1,4-dithiin 4. As 1,6-anhydro derivatives 3 are obtained, dithioethylene bridge removal and double-bond dihydroxylation give access to protected L-allose and L-glucose in stereoselective fashion and high yields.

  DOI：

  10.1021/jo800775v