2-(Pent-4-enoylamino)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside | 172946-58-6

• 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: 2-(Pent-4-enoylamino)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-[2-(pent-4-enoylamino)ethoxy]oxan-2-yl]methyl benzoate
• CAS: 172946-58-6
• 化学式: C₄₁H₃₉NO₁₁
• 分子量: 721.761
• InChiKey: VBXNMPJNWXGRND-ZMQRHWODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(Pent-4-enoylamino)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 在 水 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以85%的产率得到2-Aminoethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

  摘要：

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.

  DOI：

  10.1021/jo00129a036
• 作为产物：
  描述：

  4-戊烯酐 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 2-(Pent-4-enoylamino)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

  摘要：

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.

  DOI：

  10.1021/jo00129a036

文献信息

• The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions
  作者：Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/jo00129a036

  日期：1995.12

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.