methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate-(2->8)-methyl (allyl 7-O-acetyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate | 1225200-02-1

• 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 (allyl 7-O-acetyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate
• CAS: 1225200-02-1
• 化学式: C₃₄H₄₈O₂₀
• 分子量: 776.743
• InChiKey: OWAORQUVMHNHJI-LZIRWJNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  54.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  239.48
• 氢给体数：
  0.0
• 氢受体数：
  20.0

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 (allyl 7-O-acetyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 0.75h， 以82%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 7-O-acetyl-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
• 作为产物：
  描述：

  (2R,3R,4R,6R)-6-((R)-2-((3aR,4R,6R,7aR)-6-(allyloxy)-6-(methoxycarbonyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)-2-hydroxyethoxy)-2-((R)-1,2-diacetoxyethyl)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl diacetate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 15.0h， 以36 mg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 7-O-acetyl-3-deoxy-4,5-O-isopropylidene-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