methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(2-thiazolyl)prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate | 947152-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(2-thiazolyl)prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate
• 英文别名: methyl (2R,3R,4S)-3-acetamido-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-4-[3-(1,3-thiazol-2-yl)prop-2-ynoxy]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 947152-14-9
• 化学式: C₂₁H₂₆N₂O₈S
• 分子量: 466.512
• InChiKey: IIFSRQXBHVGILL-RSACRBQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

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-(2-thiazolyl)prop-2-ynyl]-D-glycero-D-galacto-non-2-enonate 在 溶剂黄146 作用下， 反应 1.0h， 以83%的产率得到methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(2-thiazolyl)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：

  2-溴噻唑 、 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate 在 双(乙腈)氯化钯(II) copper diacetate 、 二异丙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以59%的产率得到methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(2-thiazolyl)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