4-O-benzyl-2,3:5,6-di-O-cyclohexylidene-D-mannose diethyl dithioacetal | 798561-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-benzyl-2,3:5,6-di-O-cyclohexylidene-D-mannose diethyl dithioacetal
• CAS: 798561-19-0
• 化学式: C₂₉H₄₄O₅S₂
• 分子量: 536.797
• InChiKey: AOUSVGHHEWMZSU-XPGKHFPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-O-benzyl-2,3:5,6-di-O-cyclohexylidene-D-mannose diethyl dithioacetal 在 甲基碘化镁 、 碘 、 sodium hydride 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 18.5h， 生成 (Z)-3-[(2R,3R)-3-((R)-Benzyloxy-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-methyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-2-hydroxy-acrylic acid methyl ester
  参考文献：
  名称：

  Chloroglycidate Synthesis of a Precursor of Natural 3-Deoxy-D-manno-octulosonic Acid with Combined Protective Groups

  摘要：

  A new oxo form of D-mannose with cyclohexylidene and benzyl protective groups is synthesized with the aim of adapting the chloroglycidate synthesis for natural 3-deoxy-D-manno-octulosonic acid. The sites of fixation of the protective groups were established by converting a model compound, 4-O-acetyl-2,3: 5,6-di-O-cyclohexylidene-aldehydO-D-mannose, into a known dicyclohexylidene-D-manno-furanose. The oxo form was reacted with methyl dichloroacetate to obtain a stereoisomeric mixture of chloroglycidates which were transformed into the corresponding pyruvate. The ketone and enol forms of the latter compound were isolated and separately characterized.

  DOI：

  10.1023/b:rugc.0000025507.24993.c6
• 作为产物：
  描述：

  D-mannose diethyl dithioacetal 在 硫酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.75h， 生成 4-O-benzyl-2,3:5,6-di-O-cyclohexylidene-D-mannose diethyl dithioacetal
  参考文献：
  名称：

  Chloroglycidate Synthesis of a Precursor of Natural 3-Deoxy-D-manno-octulosonic Acid with Combined Protective Groups

  摘要：

  A new oxo form of D-mannose with cyclohexylidene and benzyl protective groups is synthesized with the aim of adapting the chloroglycidate synthesis for natural 3-deoxy-D-manno-octulosonic acid. The sites of fixation of the protective groups were established by converting a model compound, 4-O-acetyl-2,3: 5,6-di-O-cyclohexylidene-aldehydO-D-mannose, into a known dicyclohexylidene-D-manno-furanose. The oxo form was reacted with methyl dichloroacetate to obtain a stereoisomeric mixture of chloroglycidates which were transformed into the corresponding pyruvate. The ketone and enol forms of the latter compound were isolated and separately characterized.

  DOI：

  10.1023/b:rugc.0000025507.24993.c6