(3aS,4R,6R,7S,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-(4-methoxyphenyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran | 1351958-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3aS,4R,6R,7S,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-(4-methoxyphenyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 1351958-12-7
• 化学式: C₂₀H₂₇IO₆
• 分子量: 490.335
• InChiKey: ZUFZHFSUSGLMFF-HVKXIDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6R,7S,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-(4-methoxyphenyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.75h， 生成
  参考文献：
  名称：

  Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo Glycoside Synthesis

  摘要：

  A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-beta-D-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding beta-Kdo glycosides. A mechanism for the stereoselective formation of beta-D-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.

  DOI：

  10.1021/jo201531j
• 作为产物：
  描述：

  在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以22.3%的产率得到(3aS,4R,6R,7S,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-(4-methoxyphenyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
  参考文献：
  名称：

  Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo Glycoside Synthesis

  摘要：

  A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-beta-D-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding beta-Kdo glycosides. A mechanism for the stereoselective formation of beta-D-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.

  DOI：

  10.1021/jo201531j