pent-4-enyl 3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside | 189218-61-9

• 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-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-pent-4-enoxy-5-(pent-4-enoylamino)-3-phenylmethoxyoxan-4-yl] benzoate
• CAS: 189218-61-9
• 化学式: C₃₀H₃₇NO₇
• 分子量: 523.626
• InChiKey: APRORLVSGOCKJX-QFLFCSHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 、 乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-amino-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
• 作为产物：
  描述：

  Pent-4-enyl 3,4,6-tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside 在 吡啶 、 sodium methylate 、 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 10.33h， 生成 pent-4-enyl 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

文献信息

• Studies toward Lipid A:  Synthesis of Differentially Protected Disaccharide Fragments
  作者：Sian L. Griffiths、Robert Madsen、Bert Fraser-Reid

  DOI：10.1021/jo961668s

  日期：1997.5.1

  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.