(1S,8S,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene | 1040186-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,8S,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene
• CAS: 1040186-17-1
• 化学式: C₁₅H₁₆O₃S₂
• 分子量: 308.422
• InChiKey: DUWBUAWNXZJBOQ-HUBLWGQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,8S,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene 在 镍 作用下， 以 四氢呋喃 、 水 为溶剂， 以82%的产率得到1,6-anhydro-4-O-benzyl-2,3-dideoxy-β-L-erythro-pyranose
  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：

  6-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethoxymethyl]-2,3-dihydro-1,4-dithiine-5-carbaldehyde 在 Amberlyst 15 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 以94%的产率得到(1S,8S,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene
  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

文献信息

• Rapid Access to 1,6-Anhydro-β-<scp>l</scp>-hexopyranose Derivatives via Domino Reaction: Synthesis of <scp>l</scp>-Allose and <scp>l</scp>-Glucose
  作者：Daniele D’Alonzo、Annalisa Guaragna、Carmela Napolitano、Giovanni Palumbo

  DOI：10.1021/jo800775v

  日期：2008.7.1

  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.