ethyl [2,6-di-O-benzoyl-3,4-O-(1-bromomethylethylidene)-β-D-galactopyranosyl]-(1->4)-(2,3,6-tri-O-benzoyl-β-D-glucopyranozyl)-(1->6)-[(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 866885-64-5

• 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: ethyl [2,6-di-O-benzoyl-3,4-O-(1-bromomethylethylidene)-β-D-galactopyranosyl]-(1->4)-(2,3,6-tri-O-benzoyl-β-D-glucopyranozyl)-(1->6)-[(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS: 866885-64-5
• 化学式: C₁₀₀H₈₈BrNO₃₀S
• 分子量: 1895.76
• InChiKey: IVQOLJFDQMAKPR-ZJPDXZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.27
• 重原子数：
  133.0
• 可旋转键数：
  32.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  377.38
• 氢给体数：
  1.0
• 氢受体数：
  31.0

反应信息

• 作为反应物：
  描述：

  ethyl [2,6-di-O-benzoyl-3,4-O-(1-bromomethylethylidene)-β-D-galactopyranosyl]-(1->4)-(2,3,6-tri-O-benzoyl-β-D-glucopyranozyl)-(1->6)-[(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Block Synthesis of Streptococcus pneumoniae Type 14 Capsular Polysaccharide Structures*

  摘要：

  Synthesis of a thioglycoside tetrasaccharide block, beta-D-Galp-(1 -> 4)-beta-DGlcp-(1 -> 6)-[beta-D-Galp-(1 -> 4)]-beta-D-GlcNPhthp-(1 -> SEt, corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS is described. Coupling of this block with a spacer followed by removal of an isopropylidene acetal yielded an acceptor, which was elongated with the donor block to give a protected dimer of the repeating unit. Iteration of this methodology yielded the trimer. Deprotection then produced an octa and a dode-casaccharide derivative ready for conjugation to proteins to afford immunoactive glycoconjugates.

  DOI：

  10.1081/car-200066935
• 作为产物：
  描述：

  [2,6-di-O-benzoyl-3,4-O-(1-bromomethylethylidene)-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl bromide 、 ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到ethyl [2,6-di-O-benzoyl-3,4-O-(1-bromomethylethylidene)-β-D-galactopyranosyl]-(1->4)-(2,3,6-tri-O-benzoyl-β-D-glucopyranozyl)-(1->6)-[(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Block Synthesis of Streptococcus pneumoniae Type 14 Capsular Polysaccharide Structures*

  摘要：

  Synthesis of a thioglycoside tetrasaccharide block, beta-D-Galp-(1 -> 4)-beta-DGlcp-(1 -> 6)-[beta-D-Galp-(1 -> 4)]-beta-D-GlcNPhthp-(1 -> SEt, corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS is described. Coupling of this block with a spacer followed by removal of an isopropylidene acetal yielded an acceptor, which was elongated with the donor block to give a protected dimer of the repeating unit. Iteration of this methodology yielded the trimer. Deprotection then produced an octa and a dode-casaccharide derivative ready for conjugation to proteins to afford immunoactive glycoconjugates.

  DOI：

  10.1081/car-200066935