Pent-4-enyl 3,4,6-tri-O-acetyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside | 163926-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Pent-4-enyl 3,4,6-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-pent-4-enoxy-5-(pent-4-enoylamino)oxan-2-yl]methyl acetate
• CAS: 163926-96-3
• 化学式: C₂₂H₃₃NO₉
• 分子量: 455.505
• InChiKey: IJMDNZWBZYLKFR-MSEOUXRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 sodium hydride 、 乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.33h， 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：

  4-戊烯-1-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 1.0h， 以66%的产率得到Pent-4-enyl 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

• 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
• Tetrachlorophthalimido- and Pent-4-enoyl-Protected Glucosamines as Precursors for Preparation of 2-Azido-2-deoxyglucopyranosyl Building Blocks
  作者：Lars Olsson、Zhaozhong J. Jia、Bert Fraser-Reid

  DOI：10.1021/jo980427c

  日期：1998.5.1