p-Methoxybenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside | 172946-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Methoxybenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-[(4-methoxyphenyl)methoxy]-5-(pent-4-enoylamino)oxan-2-yl]methyl acetate
• CAS: 172946-65-5
• 化学式: C₂₅H₃₃NO₁₀
• 分子量: 507.538
• InChiKey: WVJUVROUONVTQL-KUEHFBCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-Methoxybenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside 在 sodium methylate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、6.67 kPa 条件下， 反应 3.0h， 生成 p-Methoxybenzyl 4,6-O-benzylidene-2-deoxy-2-(pent-4-enoylamino)-β-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：

  4-甲氧基苄醇 、 3,4,6-Tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-α-D-glucopyranosyl chloride 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以47%的产率得到p-Methoxybenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-β-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

文献信息

• Bromination of Alkenyl Glycosides with Copper(II) Bromide and Lithium Bromide:  Synthesis, Mechanism, and DFT Calculations
  作者：Robert Rodebaugh、John S. Debenham、Bert Fraser-Reid、James P. Snyder

  DOI：10.1021/jo9718509

  日期：1999.3.1