trans-2,3,4,6-tetra-O-acetyl-1-deoxy-1-(prop-1'-enyl)-β-D-galactopyranose | 903873-48-3

• 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: trans-2,3,4,6-tetra-O-acetyl-1-deoxy-1-(prop-1'-enyl)-β-D-galactopyranose
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-[(E)-prop-1-enyl]oxan-2-yl]methyl acetate
• CAS: 903873-48-3
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: HRYHAUJVZHFTNE-GFLOVTCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  trans-2,3,4,6-tetra-O-acetyl-1-deoxy-1-(prop-1'-enyl)-β-D-galactopyranose 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到(2R,3R,4R,5R,6S,E)-2-(hydroxymethyl)-6-(prop-1-enyl)-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
• 作为产物：
  描述：

  3-(1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)prop-1-ene 在 cyclooctadiene-bis(methyldiphenylphosphine)-iridium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以92%的产率得到trans-2,3,4,6-tetra-O-acetyl-1-deoxy-1-(prop-1'-enyl)-β-D-galactopyranose
  参考文献：
  名称：

  Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization of C-Allyl Glycosides

  摘要：

  Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (Z)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph2MeP)(2)Ir(cod)PF6]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism.

  DOI：

  10.1021/ol060671n