(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((1-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1071474-18-4

• 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: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((1-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1071474-18-4
• 化学式: C₃₁H₄₁N₃O₁₈S
• 分子量: 775.742
• InChiKey: ZAFWWOMTZFWQPY-VBEVKOTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  259.57
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((1-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到
  参考文献：
  名称：

  Synthesis of stable and selective inhibitors of human galectins-1 and -3

  摘要：

  The syntheses of glycolytically stable galactosides and lactosides have been made toward the selective inhibition of human galectins-1 and -3. Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation (Sonogashira, Suzuki, Heck, Glaser). Additionally, Hantzsch condensation was used to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents. Moreover, dimeric galactosides and lactosides bearing triazoles, regiospeci.cally prepared using copper-catalyzed Huisgen azide-alkyne [1,3]-dipolar cycloaddition, provided efficient galectins-1 and -3 inhibitors. Best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15 with inhibitory potency of 313 mu M against galectin-1 and best dimers were bis-lactoside 68 and 75 having both inhibitory properties of 160 mu M against Galectin-3. (c) 2008 Elsevier Ltd. All rights reserved..

  DOI：

  10.1016/j.bmc.2008.06.044
• 作为产物：
  描述：

  propargyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 、 1-叠氮-1-脱氧-β-D-吡喃半乳糖苷四乙酸酯 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以88%的产率得到(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((1-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of stable and selective inhibitors of human galectins-1 and -3

  摘要：

  The syntheses of glycolytically stable galactosides and lactosides have been made toward the selective inhibition of human galectins-1 and -3. Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation (Sonogashira, Suzuki, Heck, Glaser). Additionally, Hantzsch condensation was used to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents. Moreover, dimeric galactosides and lactosides bearing triazoles, regiospeci.cally prepared using copper-catalyzed Huisgen azide-alkyne [1,3]-dipolar cycloaddition, provided efficient galectins-1 and -3 inhibitors. Best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15 with inhibitory potency of 313 mu M against galectin-1 and best dimers were bis-lactoside 68 and 75 having both inhibitory properties of 160 mu M against Galectin-3. (c) 2008 Elsevier Ltd. All rights reserved..

  DOI：

  10.1016/j.bmc.2008.06.044