p-tolyl 6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside | 1005398-09-3

• 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: p-tolyl 6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-2-(acetyloxymethyl)-4,5-dibenzoyloxy-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1005398-09-3
• 化学式: C₃₆H₃₂O₉S
• 分子量: 640.711
• InChiKey: RDMVXUMBERKACZ-DOGNGCIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-tolyl 6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation

  摘要：

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.

  DOI：

  10.1021/ol702743x
• 作为产物：
  描述：

  4-甲苯硫酚 、 1,6-di-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到p-tolyl 6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation

  摘要：

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.

  DOI：

  10.1021/ol702743x

文献信息

• Concise assembly of linear α(1→6)-linked octamannan fluorescent probe
  作者：Mohammad S. Aqueel、Vibha Pathak、Ashish K. Pathak

  DOI：10.1016/j.tetlet.2008.09.164

  日期：2008.12

  Synthesis of a fluorescently labelled (dansylated) linear alpha(1-->6)-linked octamannan, using glycosyl fluoride donors and thioglycosyl acceptors is described. A selective and convergent two-stage activation progression was executed to construct di-, tetra and octa-mannosyl thioglycosides in three glycosylation steps with excellent yield. Further a 5-N,N-Dimethylaminonaphthalene-1-sulfonamidoethyl

  合成的荧光标记 (dansylated) 线性 alpha(1-->6)-链接八甘露聚糖，使用糖基氟供体和 thioglycosyl 受体进行描述。执行选择性和收敛的两阶段活化进程，以在三个糖基化步骤中以优异的产率构建二、四和八甘露糖基硫糖苷。此外，5-N,N-二甲基氨基萘-1-磺酰氨基乙基（丹磺酰基）与1-叠氮乙基八甘露糖硫糖苷偶联。耦合产品的全局脱保护提供了所需的丹磺酰化同源线性 alpha(1-->6)-链接八甘露聚糖。
• Vaccine Compositions For Marburg Virus
  申请人：Pathak Ashish Kumar

  公开号：US20120136142A1

  公开（公告）日：2012-05-31

  Methods and immunogenic compositions for generating an immune response against Marburg virus are provided. The immunogenic composition includes antigens obtained from a Marburg viral strain in combination with an oleanolic acid triterpene adjuvant.

  本发明提供了用于产生针对马尔堡病毒的免疫反应的方法和免疫原组合物。该免疫原组合物包括从马尔堡病毒株中获得的抗原，结合油酸三萜佐酸类佐剂。
• Imidazolium Cation Supported Solution-Phase Assembly of Homolinear α(1→6)−Linked Octamannoside: An Efficient Alternate Approach for Oligosaccharide Synthesis
  作者：Charu K. Yerneni、Vibha Pathak、Ashish K. Pathak

  DOI：10.1021/jo901169u

  日期：2009.8.21

  An efficient, simple convergent assembly of a homolinear alpha(1 -> 6)-linked octamannosyl thioglycoside was obtained starting from imidazolium cation-tagged mannosyl fluoride and thiomannoside using block couplings. During chain elongation glycosylation reactions no column chromatographic purifications were used.