methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(5'-formyl-2'-furyl)-prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate | 947152-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(5'-formyl-2'-furyl)-prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate
• CAS: 947152-26-3
• 化学式: C₂₃H₂₇NO₁₀
• 分子量: 477.468
• InChiKey: ASCUOPGRVUSKPU-OUJGAGHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  142.76
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(5'-formyl-2'-furyl)-prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate 在 溶剂黄146 作用下， 反应 1.0h， 以91%的产率得到methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(5'-formyl-2'-furyl)prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction

  摘要：

  To explore new inhibitors of the sialidase of human parainfluenza virus type 1 (hPIV-1), a series of novel Neu5Ac2en derivatives were synthesized. Thus, 8,9-O-isopropylidene-4-O-2-propynyl-Neu5Ac2en methyl ester 8 was subjected to a Sonogashira coupling reaction with a variety of heteroaryl halides to produce a series of 4-O-(3-heteroaryl-2-propynyl) compound 9. Treatment of 9 with 80% acetic acid followed by alkaline hydrolysis afforded deprotected Neu5Ac2en compounds. The 4-epi-analogs of this type of Neu5Ac2en were synthesized in a similar manner. Compound 5d showed the most potent inhibitory activity (IC50 1.2 mu M) against hPIV-1 sialidase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.049
• 作为产物：
  描述：

  methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate 、 5-溴-2-呋喃甲醛 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 以49%的产率得到methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(5'-formyl-2'-furyl)-prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction

  摘要：

  To explore new inhibitors of the sialidase of human parainfluenza virus type 1 (hPIV-1), a series of novel Neu5Ac2en derivatives were synthesized. Thus, 8,9-O-isopropylidene-4-O-2-propynyl-Neu5Ac2en methyl ester 8 was subjected to a Sonogashira coupling reaction with a variety of heteroaryl halides to produce a series of 4-O-(3-heteroaryl-2-propynyl) compound 9. Treatment of 9 with 80% acetic acid followed by alkaline hydrolysis afforded deprotected Neu5Ac2en compounds. The 4-epi-analogs of this type of Neu5Ac2en were synthesized in a similar manner. Compound 5d showed the most potent inhibitory activity (IC50 1.2 mu M) against hPIV-1 sialidase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.049