(2R,2'R,3R,3'R,4S,4'S,5R,5'R,6S,6'S)-6,6'-((1,4-phenylenebis(prop-2-yne-3,1-diyl))bis(sulfanediyl))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol) | 1071474-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,2'R,3R,3'R,4S,4'S,5R,5'R,6S,6'S)-6,6'-((1,4-phenylenebis(prop-2-yne-3,1-diyl))bis(sulfanediyl))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
• CAS: 1071474-03-7
• 化学式: C₂₄H₃₀O₁₀S₂
• 分子量: 542.628
• InChiKey: ZYVQDEYSGAZIAV-VLLPDFJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  180.3
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[3-[4-[3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylprop-1-ynyl]phenyl]prop-2-ynylsulfanyl]oxan-2-yl]methyl acetate 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到(2R,2'R,3R,3'R,4S,4'S,5R,5'R,6S,6'S)-6,6'-((1,4-phenylenebis(prop-2-yne-3,1-diyl))bis(sulfanediyl))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
  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