methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl ((4-methoxycarbonyl)-3-(E)-buten-1-yl 4,5,7-tri-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate | 932016-44-9

• 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: methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl ((4-methoxycarbonyl)-3-(E)-buten-1-yl 4,5,7-tri-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate
• CAS: 932016-44-9
• 化学式: C₃₈H₅₂O₂₄
• 分子量: 892.816
• InChiKey: PCROTIYMVPEPGX-ODQRJUDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.39
• 重原子数：
  62.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  299.92
• 氢给体数：
  0.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl ((4-methoxycarbonyl)-3-(E)-buten-1-yl 4,5,7-tri-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of spacer-containing chlamydial disaccharides as analogues of the α-Kdop-(2→8)-α-Kdop-(2→4)-α-Kdop trisaccharide epitope

  摘要：

  On the basis of high-resolution crystal structures of the antigen binding fragment of the chlamydia-specific monoclonal antibody S25-2 in complex with the trisaccharide alpha-Kdop-(2 8)-alpha-Kdop-(2 -> 4)-alpha-Kdop and part structures thereof, seven modified alpha-Kdop-(2 -> 8)-alpha-Kdop disaccharide derivatives were synthesized starting from the protected disaccharide allyl ketoside 1. Hydroboration and subsequent oxidation as well as ozonolysis, respectively, followed by Wittig-reaction for chain elongation were used to install a terminal carboxylic group on spacer entities of various chain lengths. Furthermore, addition of methyl 2-thioacetate to the allyl group furnished the corresponding thioether derivative. Standard deprotection gave the target disaccharides as simplified trisaccharide analogues, which will be used to probe the contribution of the proximal carboxylic group in the binding of chlamydia-specific di- and trisaccharide-reactive monoclonal antibodies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.003
• 作为产物：
  描述：

  methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl (3-oxoprop-1-yl 4,5,7-tri-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 、 甲氧羰基亚甲基三苯基正膦 以 四氢呋喃 为溶剂， 反应 22.0h， 以89%的产率得到methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl ((4-methoxycarbonyl)-3-(E)-buten-1-yl 4,5,7-tri-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate
  参考文献：
  名称：

  Synthesis of spacer-containing chlamydial disaccharides as analogues of the α-Kdop-(2→8)-α-Kdop-(2→4)-α-Kdop trisaccharide epitope

  摘要：

  On the basis of high-resolution crystal structures of the antigen binding fragment of the chlamydia-specific monoclonal antibody S25-2 in complex with the trisaccharide alpha-Kdop-(2 8)-alpha-Kdop-(2 -> 4)-alpha-Kdop and part structures thereof, seven modified alpha-Kdop-(2 -> 8)-alpha-Kdop disaccharide derivatives were synthesized starting from the protected disaccharide allyl ketoside 1. Hydroboration and subsequent oxidation as well as ozonolysis, respectively, followed by Wittig-reaction for chain elongation were used to install a terminal carboxylic group on spacer entities of various chain lengths. Furthermore, addition of methyl 2-thioacetate to the allyl group furnished the corresponding thioether derivative. Standard deprotection gave the target disaccharides as simplified trisaccharide analogues, which will be used to probe the contribution of the proximal carboxylic group in the binding of chlamydia-specific di- and trisaccharide-reactive monoclonal antibodies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.003