pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1->6)-3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside | 189218-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1->6)-3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-2-[[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-2-yl]oxymethyl]-6-pent-4-enoxy-5-(pent-4-enoylamino)-3-phenylmethoxyoxan-4-yl] benzoate
• CAS: 189218-66-4
• 化学式: C₅₀H₅₂Cl₄N₂O₁₆
• 分子量: 1078.78
• InChiKey: RPXYYZPNIFFWCJ-KGEUDFSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  72
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  218
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1->6)-3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.13h， 以71%的产率得到pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1->6)-3-O-benzoyl-4-O-benzyl-2-deoxy-2-amino-β-D-glucopyranoside
  参考文献：
  名称：

  Studies toward Lipid A:  Synthesis of Differentially Protected Disaccharide Fragments

  摘要：

  Disaccharides containing two glucosamine units are readily synthesized where the two amine functionalities are orthogonally protected as the tetrachlorophthaloyl and pent-4-enoyl moieties. The 1-->6 linked disaccharide has the potential to be developed toward a series of biologically interesting lipid A analogs.

  DOI：

  10.1021/jo961668s
• 作为产物：
  描述：

  pent-4-enyl 3,6-di-O-benzoyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside 在 sodium methylate 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.33h， 生成 pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1->6)-3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Studies toward Lipid A:  Synthesis of Differentially Protected Disaccharide Fragments

  摘要：

  Disaccharides containing two glucosamine units are readily synthesized where the two amine functionalities are orthogonally protected as the tetrachlorophthaloyl and pent-4-enoyl moieties. The 1-->6 linked disaccharide has the potential to be developed toward a series of biologically interesting lipid A analogs.

  DOI：

  10.1021/jo961668s