8-phthalimido-3,6-dioxaoctyl 4-O-(3,4-di-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside | 733051-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-phthalimido-3,6-dioxaoctyl 4-O-(3,4-di-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: 2-[2-[2-[2-[(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]ethoxy]ethyl]isoindole-1,3-dione
• CAS: 733051-83-7
• 化学式: C₂₉H₄₁NO₁₅
• 分子量: 643.642
• InChiKey: GJVCDBPJBODZGU-MROBIRLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  212
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  8-phthalimido-3,6-dioxaoctyl 4-O-(3,4-di-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 三氟乙酸 、 silver(l) oxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 8-phthalimido-3,6-dioxaoctyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Unexpected reductions of glycosyl spacer-armed phthalimides

  摘要：

  An unusual reductive ring-opening reaction in the title compounds, of the phthalimide group with sodium hydride in anhydrous DMF is observed for the first time and the presumed mechanism is described in detail, An unexpected hydrogenation of the phthalimide group was also observed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.028
• 作为产物：
  描述：

  8-phthalimido-3,6-dioxaoctyl 4-O-(β-D-galactooyranosyl)-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 8-phthalimido-3,6-dioxaoctyl 4-O-(3,4-di-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Unexpected reductions of glycosyl spacer-armed phthalimides

  摘要：

  An unusual reductive ring-opening reaction in the title compounds, of the phthalimide group with sodium hydride in anhydrous DMF is observed for the first time and the presumed mechanism is described in detail, An unexpected hydrogenation of the phthalimide group was also observed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.028

文献信息

• Unexpected reductions of glycosyl spacer-armed phthalimides
  作者：Xiang-Bao Meng、Hui Li、Qing-Hua Lou、Meng-Shen Cai、Zhong-Jun Li

  DOI：10.1016/j.carres.2004.03.028

  日期：2004.6

  An unusual reductive ring-opening reaction in the title compounds, of the phthalimide group with sodium hydride in anhydrous DMF is observed for the first time and the presumed mechanism is described in detail, An unexpected hydrogenation of the phthalimide group was also observed. (C) 2004 Elsevier Ltd. All rights reserved.