Methyl <2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl bromide>uronate | 101331-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl <2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl bromide>uronate
• CAS: 101331-85-5
• 化学式: C₂₅H₃₃BrO₁₇
• 分子量: 685.431
• InChiKey: QVQAJLHMVOZHQK-JVRJXXAMSA-N

物化性质

• 沸点：
  642.7±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  Methyl <2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl bromide>uronate 在 甲醇 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 (2S,3S,4S,5R,6R)-6-Allyloxy-3,5-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  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：

  Methyl 1,2,4-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranuronate 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 以81.5%的产率得到Methyl <2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl bromide>uronate
  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