(R,S)-2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 149820-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,S)-2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(oxiran-2-ylmethoxy)oxan-2-yl]methyl acetate
• CAS: 149820-55-3
• 化学式: C₁₇H₂₄O₁₁
• 分子量: 404.371
• InChiKey: JAELXEUVWSMEOF-HUVXYLLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R,S)-2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-O-(β-galactopyranosyl)-rac-glycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465
• 作为产物：
  描述：

  allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(R,S)-2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• Multifunctional multivalency: a focused library of polymeric cholera toxin antagonists
  作者：Huu-Anh Tran、Pavel I. Kitov、Eugenia Paszkiewicz、Joanna M. Sadowska、David R. Bundle

  DOI：10.1039/c0ob01089h

  日期：——

  the multivalent ligands is important for successful interaction with multimeric proteins. Polymer-based heterobifunctional ligands that contain pendant groups prearranged into heterodimers can be used to probe the active site and surrounding area of the receptor. Here we describe the synthesis and activities of a series of galactose conjugates on polyacrylamide and dextran. Conjugation of a second fragment

  多价配体的结构预组织对于与多聚体蛋白成功相互作用很重要。包含预先排列成异二聚体的侧基的基于聚合物的异双功能配体可用于探测受体的活性位点和周围区域。在这里，我们描述了一系列半乳糖结合物对聚丙烯酰胺和葡聚糖的合成和活性。第二个片段的缀合导致霍乱毒素的纳摩尔抑制剂，而仅半乳糖的祖细胞显示没有可检测的活性。