Allyl β-cellobiosiduronic acid | 93706-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl β-cellobiosiduronic acid
• CAS: 93706-54-8
• 化学式: C₁₅H₂₄O₁₂
• 分子量: 396.348
• InChiKey: JYQWVKQWBQJUNP-HOQIFGSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.09
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  195.6
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  allyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 chromium(VI) oxide 、 氢氧化钾 、 乙醇 、 硫酸 、 高氯酸,吡啶 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 水 、 丙酮 为溶剂， 反应 23.5h， 生成 Allyl β-cellobiosiduronic acid
  参考文献：
  名称：

  Two synthetic antigens related to Streptococcus pneumoniae type 3 capsular polysaccharide

  摘要：

  The synthesis of the allyl beta-glycosides (8 and 20, respectively) of beta-D-GlcpA-(1----4)-D-Glcp and beta-D-Glcp-(1----3)-D-GlcpA (overlapping disaccharide fragments A and B) in the linear chain of the capsular polysaccharide (S3) from Streptococcus pneumoniae type 3 is described. Oxidation of allyl 2,3,6,2',3',4'-hexa-O-acetyl-beta-cellobioside with chromic acid and saponification of the product gave 8. The synthesis of 20 involved glycosylation of methyl 5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranuronate or its 3-O-trityl derivative and subsequent furanose----pyranose transformation. The derivatives 8 and 20 were each copolymerised with acrylamide. In serological tests (enzyme immunoassay and passive hemagglutination), the resulting antigens exhibited the specificity of S3. It was concluded that fragment A was a much stronger immunodeterminant than fragment B.

  DOI：

  10.1016/s0008-6215(00)90452-x