methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate | 909103-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-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-prop-2-ynoxy-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 909103-59-9
• 化学式: C₁₈H₂₅NO₈
• 分子量: 383.398
• InChiKey: NXSDYYIDPOIJHG-CWCFIDOXSA-N

物化性质

• 沸点：
  583.9±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

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-(2-propynyl)-D-glycero-D-galacto-non-2-enonate 在 copper(l) iodide 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(diethylamino)-3-(methylsulfonylimino)propoxy]-D-glycero-D-galactonon-2-enonic acid methyl ester
  参考文献：
  名称：

  Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1

  摘要：

  Eleven novel sialidase inhibitors 9 and 10 with an N-sulfonylamidino group at the C-4 position of Neu 5Ac2en 1 against human parainfluenza virus type 1 (hPIV-1) were synthesized using copper-catalyzed three-component coupling reactions, and their inhibitory activities against hPIV-1 sialidase were studied. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.010
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 吡啶 、 甲醇 、 15-冠醚-5 、 sodium methylate 、 三苯基膦氢溴酸盐 、 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.25h， 生成 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1

  摘要：

  Eleven novel sialidase inhibitors 9 and 10 with an N-sulfonylamidino group at the C-4 position of Neu 5Ac2en 1 against human parainfluenza virus type 1 (hPIV-1) were synthesized using copper-catalyzed three-component coupling reactions, and their inhibitory activities against hPIV-1 sialidase were studied. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.010

文献信息

• Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction
  作者：Kazuki Sato、Kiyoshi Ikeda、Takashi Suzuki、Shinya Aoyama、Naoyoshi Maki、Yasuo Suzuki、Masayuki Sato

  DOI：10.1016/j.tet.2007.05.049

  日期：2007.8

  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.
• 2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogues structurally modified at the C-4 position: Synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1
  作者：Kiyoshi Ikeda、Kazuki Sato、Satoru Kitani、Takashi Suzuki、Naoyoshi Maki、Yasuo Suzuki、Masayuki Sato

  DOI：10.1016/j.bmc.2006.07.045

  日期：2006.12

  To explore the influence of binding to human parainfluenza virus type 1 (hPIV-1), a series of 4-O-substituted Neu5Ac2en derivatives 6a-e was synthesized and tested for their ability to inhibit hPIV-1 sialidase. Among compounds 6a-e, the 4-O-ethyl-Neu5Ac2en derivative 6b showed the most potent inhibitory activity (IC50 6.3 microM) against hPIV-1 sialidase.