Methyl 3-O-β-D-glucopyranosyl-1,2-O-isopropylidene-α-D-glucofuranuronate | 101331-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-O-β-D-glucopyranosyl-1,2-O-isopropylidene-α-D-glucofuranuronate
• CAS: 101331-81-1
• 化学式: C₁₆H₂₆O₁₂
• 分子量: 410.375
• InChiKey: WEWKJKDSRKFHAK-MWXIIINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.42
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  173.6
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Methyl 3-O-β-D-glucopyranosyl-1,2-O-isopropylidene-α-D-glucofuranuronate 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 Methyl 3-O-β-D-glucopyranosyl-D-glucopyranuronate
  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
• 作为产物：
  描述：

  3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose 在 甲醇 、 sodium methylate 、 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 Methyl 3-O-β-D-glucopyranosyl-1,2-O-isopropylidene-α-D-glucofuranuronate
  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