phenyl 2,3,4,6-tetra-S,O,O,O-acetyl-1,2-dithio-α-D-mannopyranoside | 240811-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-S,O,O,O-acetyl-1,2-dithio-α-D-mannopyranoside
• CAS: 240811-30-7
• 化学式: C₂₀H₂₄O₈S₂
• 分子量: 456.538
• InChiKey: DQQHNPDDNIOUJS-SWBPCFCJSA-N

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：

  N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 、 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 24.0h， 以25%的产率得到methyl 3-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-sulfanyloxan-2-yl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  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：

  在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 36.5h， 生成 phenyl 2,3,4,6-tetra-S,O,O,O-acetyl-1,2-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