3,4,6-Tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-α-D-glucopyranosyl chloride | 163926-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-Tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-α-D-glucopyranosyl chloride
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-chloro-5-(pent-4-enoylamino)oxan-2-yl]methyl acetate
• CAS: 163926-98-5
• 化学式: C₁₇H₂₄ClNO₈
• 分子量: 405.832
• InChiKey: NYWHDXHJKBYHMY-NHMWIVBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-Tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-α-D-glucopyranosyl chloride 在 4 A molecular sieve 、 水 、 碘 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 Methyl 6-O-<3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl>-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  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：

  乙酰氯 、 2-Deoxy-2-(pent-4-enoylamino)-α-D-glucopyranose 反应 8.0h， 以56%的产率得到3,4,6-Tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-α-D-glucopyranosyl chloride
  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

• Two New Orthogonal Amine-Protecting Groups that can be Cleaved under Mild or Neutral Conditions
  作者：John S. Debenham、Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/ja00116a047

  日期：1995.3