2,2,4,4,6,6-Hexakis[4-(1,3-diazidopropan-2-yloxymethyl)phenoxy]-1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene | 1088354-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,4,4,6,6-Hexakis[4-(1,3-diazidopropan-2-yloxymethyl)phenoxy]-1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene
• 英文别名: 2,2,4,4,6,6-hexakis[4-(1,3-diazidopropan-2-yloxymethyl)phenoxy]-1,3,5-triaza-2λ5,4λ5,6λ5-triphosphacyclohexa-1,3,5-triene
• CAS: 1088354-69-1
• 化学式: C₆₀H₆₆N₃₉O₁₂P₃
• 分子量: 1618.36
• InChiKey: CPCQNFQFTDOSMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.9
• 重原子数：
  114
• 可旋转键数：
  54
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  320
• 氢给体数：
  0
• 氢受体数：
  39

反应信息

• 作为反应物：
  描述：

  2,2,4,4,6,6-Hexakis[4-(1,3-diazidopropan-2-yloxymethyl)phenoxy]-1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene 、 propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以84%的产率得到
  参考文献：
  名称：

  First Synthesis of “Majoral-Type” Glycodendrimers Bearing Covalently Bound α-d-Mannopyranoside Residues onto a Hexachlocyclotriphosphazene Core

  摘要：

  A short and efficient strategy for the first synthesis of "Majoral-Type" multivalent glycodendrimers bearing covalently bound alpha-D-mannopyranosides onto a cyclotriphosphazene scaffold assembled using single-step Step Sonogashira and click chemistry is reported. New glycoclusters with valencies ranging from 6 to 18 and different epitope spatial arrangements were obtained. Cross-linking abilities of this series of glycodendrimers were evaluated with the model lectin from Canavalia ensiformis (Concanavalin A). The decameric mannoside 23, built around 19, was shown to be much faster in cross-linking the tetravalent lectin Concanavalin A than the positive control, which is the polysaccharide mannan from yeast. The new glycoconjugates reported may be promising tools as probes or effectors of biological processes involving multivalent carbohydrate-binding proteins.

  DOI：

  10.1021/jo801850f
• 作为产物：
  描述：

  1,3-diazido 2-propanol 、 1,1,3,3,5,5-hexakis(4-(bromomethyl)phenoxy)cyclotriphosphazene 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.5h， 以66%的产率得到2,2,4,4,6,6-Hexakis[4-(1,3-diazidopropan-2-yloxymethyl)phenoxy]-1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene
  参考文献：
  名称：

  First Synthesis of “Majoral-Type” Glycodendrimers Bearing Covalently Bound α-d-Mannopyranoside Residues onto a Hexachlocyclotriphosphazene Core

  摘要：

  A short and efficient strategy for the first synthesis of "Majoral-Type" multivalent glycodendrimers bearing covalently bound alpha-D-mannopyranosides onto a cyclotriphosphazene scaffold assembled using single-step Step Sonogashira and click chemistry is reported. New glycoclusters with valencies ranging from 6 to 18 and different epitope spatial arrangements were obtained. Cross-linking abilities of this series of glycodendrimers were evaluated with the model lectin from Canavalia ensiformis (Concanavalin A). The decameric mannoside 23, built around 19, was shown to be much faster in cross-linking the tetravalent lectin Concanavalin A than the positive control, which is the polysaccharide mannan from yeast. The new glycoconjugates reported may be promising tools as probes or effectors of biological processes involving multivalent carbohydrate-binding proteins.

  DOI：

  10.1021/jo801850f

文献信息

• First Synthesis of “Majoral-Type” Glycodendrimers Bearing Covalently Bound α-<scp>d</scp>-Mannopyranoside Residues onto a Hexachlocyclotriphosphazene Core
  作者：Mohamed Touaibia、René Roy

  DOI：10.1021/jo801850f

  日期：2008.12.5

  A short and efficient strategy for the first synthesis of "Majoral-Type" multivalent glycodendrimers bearing covalently bound alpha-D-mannopyranosides onto a cyclotriphosphazene scaffold assembled using single-step Step Sonogashira and click chemistry is reported. New glycoclusters with valencies ranging from 6 to 18 and different epitope spatial arrangements were obtained. Cross-linking abilities of this series of glycodendrimers were evaluated with the model lectin from Canavalia ensiformis (Concanavalin A). The decameric mannoside 23, built around 19, was shown to be much faster in cross-linking the tetravalent lectin Concanavalin A than the positive control, which is the polysaccharide mannan from yeast. The new glycoconjugates reported may be promising tools as probes or effectors of biological processes involving multivalent carbohydrate-binding proteins.