methyl (allyl 7,8-O-carbonyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate | 1225199-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl (allyl 7,8-O-carbonyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate
• CAS: 1225199-99-4
• 化学式: C₁₆H₂₂O₉
• 分子量: 358.345
• InChiKey: CERZPYDQVVKFAO-JXOGKFFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (allyl 7,8-O-carbonyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 45.0h， 以98%的产率得到methyl (allyl 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
• 作为产物：
  描述：

  methyl (allyl 7,8-O-carbonyl-3-deoxy-α-D-manno-2-octulopyranosid)-onate 、 丙酮 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到methyl (allyl 7,8-O-carbonyl-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