(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 1361016-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS: 1361016-59-2
• 化学式: C₂₄H₃₀O₅S
• 分子量: 430.565
• InChiKey: QMSKITBQZSYFQH-WBKUQYDJSA-N

物化性质

• 沸点：
  593.1±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2-methyl-5-tert-butylphenyl) 2-O-benzoyl-3-O-levulinoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes

  摘要：

  Biotinylated tri and tetrasaccharide: alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man; alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man (1 -> 2) alpha Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic donors have been prepared: one for 1 -> 2 linkage and two for the 1 -> 3 linkage (protected with a 4,6-O-benzylidene or a 4,6-di-O-benzyl). The benzyliden protected one was not found reactive enough, and the benzylated donor was preferred. These biotinylated oligomanosides were evaluated as antigen in Crohn disease diagnosis and used coupled to streptavidin as hapten for eliciting polyclonal antibodies in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.048
• 作为产物：
  描述：

  D-甘露糖 在 吡啶 、 D(+)-10-樟脑磺酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes

  摘要：

  Biotinylated tri and tetrasaccharide: alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man; alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man (1 -> 2) alpha Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic donors have been prepared: one for 1 -> 2 linkage and two for the 1 -> 3 linkage (protected with a 4,6-O-benzylidene or a 4,6-di-O-benzyl). The benzyliden protected one was not found reactive enough, and the benzylated donor was preferred. These biotinylated oligomanosides were evaluated as antigen in Crohn disease diagnosis and used coupled to streptavidin as hapten for eliciting polyclonal antibodies in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.048

文献信息

• Iron(III)-Triflate-Catalyzed Multiple Glycosylations with Peracetylated β-d-Glucosamine
  作者：Amandine Xolin、Stéphanie Norsikian、François-Didier Boyer、Jean-Marie Beau

  DOI：10.1002/ejoc.201600457

  日期：2016.7

  Direct multiple glycosylations of thioaryl and propargyl mannopyranosides with peracetylated β-d-glucosamine have been carried out using catalytic iron(III) triflate as a promoter in the presence of 2,4,6-tri-tert-butylpyrimidine under microwave irradiation. This has led to the one-step formation of various oligosaccharides with mannose at the branching point. Subsequent direct introduction of a linker

  在微波辐射下，在 2,4,6-三叔丁基嘧啶存在下，使用催化三氟甲磺酸铁 (III) 作为促进剂，硫代芳基和炔丙基吡喃甘露糖苷与过乙酰化 β-d-葡糖胺进行了直接多重糖基化。这导致在分支点处一步形成具有甘露糖的各种寡糖。随后通过铜催化的叠氮化物-炔烃环加成与炔丙基支链聚糖和最终脱保护直接引入接头，从而快速获得 N-聚糖模拟物。