Ethyl (Methyl 2,6,7-trideoxy-2-iodo-3,4-isopropylidene-β-D-galacto-oct-6(Z)-eno-1,5-pyranosid)uronate | 137792-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (Methyl 2,6,7-trideoxy-2-iodo-3,4-isopropylidene-β-D-galacto-oct-6(Z)-eno-1,5-pyranosid)uronate
• 英文别名: ethyl (Z)-3-[(3aS,4R,6R,7R,7aS)-7-iodo-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]prop-2-enoate
• CAS: 137792-68-8
• 化学式: C₁₄H₂₁IO₆
• 分子量: 412.222
• InChiKey: MJQPNYZCJISHJZ-COIISXCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl (Methyl 2,6,7-trideoxy-2-iodo-3,4-isopropylidene-β-D-galacto-oct-6(Z)-eno-1,5-pyranosid)uronate 在 2,6-二甲基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 (1S,5S,6S,7R,8R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-8-hydroxy-2-oxabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Free Radical Methodology for Carbohydrate to Carbocycle Transformations: An Efficient Synthesis of the Tricyclic Dihydrofuran Portion of Azadirachtin

  摘要：

  Iodo lactone 6b, derived from D-galactal, undergoes tin hydride mediated transannular radical cyclization to give the tricyclic lactone 7, which is easily converted into an advanced precursor of the tricyclic dihydrofuran portion of the potent insect antifeedant azadirachtin (1).

  DOI：

  10.1021/jo00097a007
• 作为产物：
  描述：

  2,6-anhydro-5-deoxy-3,4-O-isopropylidene-D-arabino-hex-5-enitol 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 Ethyl (Methyl 2,6,7-trideoxy-2-iodo-3,4-isopropylidene-β-D-galacto-oct-6(Z)-eno-1,5-pyranosid)uronate
  参考文献：
  名称：

  Free Radical Methodology for Carbohydrate to Carbocycle Transformations: An Efficient Synthesis of the Tricyclic Dihydrofuran Portion of Azadirachtin

  摘要：

  Iodo lactone 6b, derived from D-galactal, undergoes tin hydride mediated transannular radical cyclization to give the tricyclic lactone 7, which is easily converted into an advanced precursor of the tricyclic dihydrofuran portion of the potent insect antifeedant azadirachtin (1).

  DOI：

  10.1021/jo00097a007

文献信息

• Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes
  作者：R. A. Alonso、G. D. Vite、R. E. McDevitt、B. Fraser-Reid

  DOI：10.1021/jo00028a033

  日期：1992.1

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.