(3aS,4R,6R,7R,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-methoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran | 1351958-16-1

• 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: (3aS,4R,6R,7R,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-methoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS: 1351958-16-1
• 化学式: C₂₁H₂₉IO₇
• 分子量: 520.362
• InChiKey: NSNZXVMIMVLAPQ-IGYPPAOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6R,7R,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-methoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以93.2%的产率得到(3aR,4R,6S,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[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
• 作为产物：
  描述：

  (3aS,4R,6R,7R,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 potassium tert-butylate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.67h， 生成 (3aS,4R,6R,7R,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-methoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[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