acetylthiopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 482593-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetylthiopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(3-acetylsulfanylpropoxy)oxan-2-yl]methyl acetate
• CAS: 482593-10-2
• 化学式: C₁₉H₂₈O₁₁S
• 分子量: 464.491
• InChiKey: IVXAJAIAQKFPMN-GFEQUFNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  acetylthiopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[3-[3-[phenyl-bis[3-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropylsulfanyl]propyl]silyl]propylsulfanyl]propoxy]oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 偶氮二异丁腈 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 56.5h， 生成 acetylthiopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090