allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-α-D-glucopyranoside | 1000599-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-α-D-glucopyranoside
• CAS: 1000599-08-5
• 化学式: C₃₃H₄₅NO₇
• 分子量: 567.723
• InChiKey: XKPMWTILEZIXIP-CTARAAFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  41.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-α-D-glucopyranoside 在 Wilkinson's catalyst 三乙烯二胺 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以75%的产率得到1-propenyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Properties of Surfactants derived fromN‐Acetyl‐D‐Glucosamine

  摘要：

  The synthesis of 2-acetamido-2-deoxy-6-O-octanoyl-D-glucono-1,5-lactone 9 and 2-acetamido-2-deoxy-6-O-octanoyl-alpha-D-glueopyranose 7 from 2-acetamido-2-deoxy-alpha-D-glucopyranose is reported. For both targets, the key intermediate was allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-alpha-D-glucopyranoside 5. Surface tension measurements (critical micellar concentration of 22.3 mM and 5 mM for 9 and 7, respectively) showed up the surface activity of both compounds, while enzyme inhibition assays indicated that 9 could inhibit bovine beta-N-acetylglucosaminidase (K-i = 6.5 mu M) but not Serratia marcescens chitobiase nor hen egg-white lysozyme. Moreover, 7 was shown to induce chitinase production of S. marcescens and to be readily metabolized by these bacteria.[GRAPHICS]

  DOI：

  10.1080/07328300701634804
• 作为产物：
  描述：

  allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside 、 辛酰氯 以 甲苯 为溶剂， 反应 4.0h， 以70%的产率得到allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Properties of Surfactants derived fromN‐Acetyl‐D‐Glucosamine

  摘要：

  The synthesis of 2-acetamido-2-deoxy-6-O-octanoyl-D-glucono-1,5-lactone 9 and 2-acetamido-2-deoxy-6-O-octanoyl-alpha-D-glueopyranose 7 from 2-acetamido-2-deoxy-alpha-D-glucopyranose is reported. For both targets, the key intermediate was allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-alpha-D-glucopyranoside 5. Surface tension measurements (critical micellar concentration of 22.3 mM and 5 mM for 9 and 7, respectively) showed up the surface activity of both compounds, while enzyme inhibition assays indicated that 9 could inhibit bovine beta-N-acetylglucosaminidase (K-i = 6.5 mu M) but not Serratia marcescens chitobiase nor hen egg-white lysozyme. Moreover, 7 was shown to induce chitinase production of S. marcescens and to be readily metabolized by these bacteria.[GRAPHICS]

  DOI：

  10.1080/07328300701634804