7-amino-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranose 7,5-(cyclic thiocarbamate) | 263328-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-amino-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranose 7,5-(cyclic thiocarbamate)
• CAS: 263328-63-8
• 化学式: C₁₁H₁₇NO₅S
• 分子量: 275.326
• InChiKey: GWRZORGXAUBKII-ANZWQOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-amino-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranose 7,5-(cyclic thiocarbamate) 在 三氟乙酸 作用下， 以 水 为溶剂， 生成 7-amino-6,7-dideoxy-α-D-gluco-heptofuranose 7,5-(cyclic thiocarbamate) 、 7-amino-6,7-dideoxy-β-D-gluco-heptofuranose 7,5-(cyclic thiocarbamate)
  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：

  6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranurononitrile 在 diborane-dimethylsulfide complex 、 三乙胺 、 calcium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.0h， 生成 7-amino-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranose 7,5-(cyclic thiocarbamate)
  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