methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl (allyl 3-deoxy-α-D-manno-oct-2-ulopyranosid)onate | 1225200-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl (allyl 3-deoxy-α-D-manno-oct-2-ulopyranosid)onate
• CAS: 1225200-03-2
• 化学式: C₂₉H₄₂O₁₉
• 分子量: 694.641
• InChiKey: CWWAZEBAWWBQLD-JOBBKGGZSA-N

物化性质

• 沸点：
  749.8±60.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.04
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  255.41
• 氢给体数：
  3.0
• 氢受体数：
  19.0

反应信息

• 作为产物：
  描述：

  methyl (allyl 3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate 、 Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)-onate 在 mercury(II) cyanide 作用下， 以 硝基甲烷 为溶剂， 反应 5.0h， 以11%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 (allyl 3-deoxy-α-D-manno-oct-2-ulopyranosid)onate
  参考文献：
  名称：

  Synthesis of a neoglycoconjugate containing a Chlamydophila psittaci-specific branched Kdo trisaccharide epitope

  摘要：

  The branched Kdo trisaccharide sodium (3-deoxy-alpha-D-manno-oct-2-ulopyranosyl)onate-(2 -> 8)-[sodium (3-deoxy-alpha-D-manno-oct-2-ulopyranosyl)onate-(2 -> 4)]-sodium (allyl 3-deoxy-alpha-D-manno-oct-2-ulopyranosid)onate has been prepared utilizing the regioselective glycosylation of the C-7, C-8 diol entity of a Kdo monosaccharide acceptor with a Kdo bromide donor followed by the attachment of the third Kdo unit to O-4 of the disaccharide intermediate. Deacetylation and hydrolysis of the methyl ester groups furnished the trisaccharide allyl glycoside which was converted into the corresponding 3-(2-aminoethylthio)propyl glycoside. Subsequent covalent attachment to bovine serum albumin furnished a neoglyco-conjugate serving as an antigen for the induction of Chlamydophila psittaci-specific monoclonal antibodies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.015