Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1-->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid | 95580-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1-->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid
• 英文别名: Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid；benzyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,2,3,6-tetra-O-benzyl-β-D-glucopyranose
• CAS: 95580-50-0
• 化学式: C₇₆H₇₉NO₂₁
• 分子量: 1342.46
• InChiKey: VZEVTUGFLUOTLZ-ZJCUOOMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  98.0
• 可旋转键数：
  30.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  244.11
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1-->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Paulsen, Hans; Hadamczyk, Doris; Kutschker, Wolfram, Liebigs Annalen der Chemie, 1985, # 1, p. 129 - 141

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 吡啶 、 2,3,5-三甲基吡啶 、 calcium sulfate 、 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 26.0h， 生成 Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1-->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid
  参考文献：
  名称：

  Paulsen, Hans; Hadamczyk, Doris; Kutschker, Wolfram, Liebigs Annalen der Chemie, 1985, # 1, p. 129 - 141

  摘要：

  DOI：

文献信息

• Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14
  作者：John A.F Joosten、Johannis P Kamerling、Johannes F.G Vliegenthart

  DOI：10.1016/s0008-6215(03)00313-6

  日期：2003.11

  tetrasaccharide repeating units of Streptococcus pneumoniae serotype 14 capsular polysaccharide. In a chemical approach, the intermediate linear trisaccharide 3 and hexasaccharide 4 were synthesized. Galactose residues were beta-(1-->4)-connected to the internal N-acetyl-beta-D-glucosamine residues by using bovine milk beta-1,4-galactosyltransferase. Both title oligosaccharides will be conjugated to carrier proteins

  化学酶合成描述了四糖β-D-Galp-（1-> 4）-β-D-Glcp-（1-> 6）-β-D-Galp-（1-> 4 ）]-beta-D-GlcpNAc-（1-> O（CH（2））（6）NH（2）（1）和八糖beta-D-Galp-（1-> 4）-beta-D -Glcp-（1-> 6）-[beta-D-Galp-（1-> 4）]-beta-D-GlcpNAc-（1-> 3）-beta-D-Galp-（1- -> 4）-beta-D-Glcp-（1-> 6）-[beta-D-Galp-（1-> 4）]-beta-D-GlcpNAc-（1-> O（CH（ 2））（6）NH（2）（2），分别代表肺炎链球菌血清型14荚膜多糖的一个和两个四糖重复单元，化学合成了中间体线性三糖3和六糖4，半乳糖残基为β-使用牛乳β-1,4-半乳糖基转移酶将（1-> 4）连接到内部N-乙酰基-β-D-葡萄糖胺残基。
• Chemo-enzymatic synthesis of tetra-, penta-, and hexasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14
  作者：John A.F Joosten、Bart J Lazet、Johannis P Kamerling、Johannes F.G Vliegenthart

  DOI：10.1016/s0008-6215(03)00292-1

  日期：2003.11

  The chemo-enzymatic synthesis is described of beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1--> O(CH2)(6)NH2 (1), beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (2), beta-D-Galp-(1 -->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (3), and beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1--> 3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->O(CH2)(6)NH2 (4), representing fragments of the repeating unit of the Streptococcuspneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk beta-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models. (C) 2003 Elsevier Ltd. All rights reserved.