phenyl 2,3,4,6-tetra-O,O,O,S-acetyl-1,6-dithio-α-D-mannopyranoside | 497149-10-7

• 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: phenyl 2,3,4,6-tetra-O,O,O,S-acetyl-1,6-dithio-α-D-mannopyranoside
• CAS: 497149-10-7
• 化学式: C₂₀H₂₄O₈S₂
• 分子量: 456.538
• InChiKey: FQSQHOMQKMIBKD-SWBPCFCJSA-N

物化性质

• 沸点：
  540.1±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O,O,O,S-acetyl-1,6-dithio-α-D-mannopyranoside 、 phenyl 2,3,4,6-tetra-S,O,O,O-acetyl-1,2-dithio-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 48.0h， 以41%的产率得到
  参考文献：
  名称：

  Oligomeric Thioglycosides with α-d-manno-(1‘→2) Linkages from a Glycal-1,2-episulfide

  摘要：

  [GRAPHICS]Under basic conditions, phenyl 1,2-dithio-alpha-D-mannopyranoside farms a glycal-1,2-episulfide, which undergoes controlled oligomerization to afford a family of thio-oligo-alpha-D-mannopyranosides in a single reaction. The episulfide can also be intercepted by added thiolates, which leads to other sorts of thioglycosides. These alpha-(1-->2)- linked thio-mannopyranosides might have application as mimics of natural structures such as viral high mannose glycoproteins or ManLAM.

  DOI：

  10.1021/ol990702x
• 作为产物：
  描述：

  Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 phenyl 2,3,4,6-tetra-O,O,O,S-acetyl-1,6-dithio-α-D-mannopyranoside
  参考文献：
  名称：

  Oligomeric Thioglycosides with α-d-manno-(1‘→2) Linkages from a Glycal-1,2-episulfide

  摘要：

  [GRAPHICS]Under basic conditions, phenyl 1,2-dithio-alpha-D-mannopyranoside farms a glycal-1,2-episulfide, which undergoes controlled oligomerization to afford a family of thio-oligo-alpha-D-mannopyranosides in a single reaction. The episulfide can also be intercepted by added thiolates, which leads to other sorts of thioglycosides. These alpha-(1-->2)- linked thio-mannopyranosides might have application as mimics of natural structures such as viral high mannose glycoproteins or ManLAM.

  DOI：

  10.1021/ol990702x