(3aR,4R,6S,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-dodecoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran | 1351958-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,4R,6S,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-dodecoxy-6-(4-methoxyphenyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS: 1351958-24-1
• 化学式: C₃₂H₅₂O₇
• 分子量: 548.761
• InChiKey: RRGBILHROXHADS-BFGNKNHRSA-N

物化性质

• 沸点：
  599.0±50.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 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 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.75h， 生成 (3aR,4R,6S,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-dodecoxy-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

文献信息

• Unexpected Anomeric Selectivity of a 1-<i>C</i>-Arylglycal Donor in Kdo Glycoside Synthesis
  作者：Yuxin Qian、Jianhao Feng、Masood Parvez、Chang-Chun Ling

  DOI：10.1021/jo201531j

  日期：2012.1.6

  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.