methyl 2,3,4-tri-O-acetyl-α-D-manno-heptopyranosidurononitrile | 263328-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-D-manno-heptopyranosidurononitrile
• 英文别名: [(2R,3R,4S,5S,6S)-4,5-diacetyloxy-2-(cyanomethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 263328-50-3
• 化学式: C₁₄H₁₉NO₈
• 分子量: 329.307
• InChiKey: SGHONMRGNOUROK-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-D-manno-heptopyranosidurononitrile 在 diborane-dimethylsulfide complex 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 生成 methyl 7-amino-6,7-dideoxy-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates

  摘要：

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.

  DOI：

  10.1016/s0008-6215(99)00273-6
• 作为产物：
  描述：

  methyl 6-deoxy-6-iodo-α-D-mannopyranoside 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 2,3,4-tri-O-acetyl-α-D-manno-heptopyranosidurononitrile
  参考文献：
  名称：

  Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates

  摘要：

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.

  DOI：

  10.1016/s0008-6215(99)00273-6