methyl 2,3-di-S,O-acetyl-4,6-O-(phenylmethylene)-2-thio-α-D-mannopyranoside | 144607-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-S,O-acetyl-4,6-O-(phenylmethylene)-2-thio-α-D-mannopyranoside
• 英文别名: Methyl 3-O,2-S-diacetyl-4,6-O-(phenylmethylene)-2-thio-α-D-mannopyranoside；methyl 4,6-O-benzylidene-2,-3-di-S,O-acetyl-α-D-mannopyranoside
• CAS: 144607-21-6
• 化学式: C₁₈H₂₂O₇S
• 分子量: 382.434
• InChiKey: UOSAJYQIARBIGQ-LMMHAMTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-S,O-acetyl-4,6-O-(phenylmethylene)-2-thio-α-D-mannopyranoside 在 吡啶 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 methyl 2,3,4,6-tetra-S,O,O,O-acetyl-2-thio-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
• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到methyl 2,3-di-S,O-acetyl-4,6-O-(phenylmethylene)-2-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Reactions of some pyranoside diol monotriflates with nucleophiles and bases

  摘要：

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.

  DOI：

  10.1021/jo00052a058