1-O-(5-isothiocyanato-3-oxapentyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 393803-25-3

• 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: 1-O-(5-isothiocyanato-3-oxapentyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[2-(2-isothiocyanatoethoxy)ethoxy]oxan-2-yl]methyl acetate
• CAS: 393803-25-3
• 化学式: C₁₉H₂₇NO₁₁S
• 分子量: 477.489
• InChiKey: ZSIIJBNOSAICBK-GFEQUFNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 、 1-O-(5-isothiocyanato-3-oxapentyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Reactivity Tournament of Isothiocyanato-Functionalized Saccharides with 1,6-Diamino-3,6-oxaoctane

  摘要：

  Thiourea-bridged glycoclusters and glycodendrimers are described in the literature as mimetics of (oligoantennary) oligosaccharides to serve as high-affinity lectin ligands. In extension of this concept, the assembly of different, structurally varied isothiocyanato-functionalized sugar derivatives on an oligoamine scaffold would lead to novel mixed glycoclusters. To control this approach, the relative reactivities of the isothiocyanates used in the thiourea-bridging reaction have to be known. Therefore, competition experiments with six different sugar isothiocyanates were carried out using 1,8-diamino-3,6-dioxaoctane as a symmetrical difunctionalized core molecule. Reactivities were ranked on the basis of integration ratios in the H-1 NMR spectra. A first mixed thiourea-bridged glycocluster was successfully prepared.

  DOI：

  10.1007/s007060200022
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 三氟化硼乙醚 、 肼 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 1-O-(5-isothiocyanato-3-oxapentyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  The Lectin-Binding Properties of Six Generations of Mannose-Functionalized Dendrimers

  摘要：

  [GRAPHICS]First- through sixth-generation PAMAM dendrimers have been functionalized with mannose residues. Characterization with MALDI-TOF MS and H-1 NMR is reported. Different binding enhancements consistent with monovalent interaction, glycoside clustering, and multivalent binding are observed for different generations of dendrimers.

  DOI：

  10.1021/ol016568+

文献信息

• WO2007/106437
  申请人：——

  公开号：——

  公开（公告）日：——