methyl α-D-gluco-heptopyranosidurononitrile | 148379-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-gluco-heptopyranosidurononitrile
• 英文别名: Methyl 6-deoxy-α-D-gluco-heptopyranurononitrile；2-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]acetonitrile
• CAS: 148379-97-9
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: DYUHUJRRDJPOAS-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α-D-gluco-heptopyranosidurononitrile 在 吡啶 、 dimethyl sulfide borane 、 氯 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 41.0h， 生成 N,N'-bis(methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-dlucopyranosid-6-yl)thiourea
  参考文献：
  名称：

  Sugar Thioureas as Anion Receptors. Effect of Intramolecular Hydrogen Bonding in the Carboxylate Binding Properties of Symmetric Sugar Thioureas

  摘要：

  DOI：

  10.1021/ol990889s
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.16h， 生成 methyl α-D-gluco-heptopyranosidurononitrile
  参考文献：
  名称：

  A mild and simple enzymic conversion of aldono- and aldurononitriles into the corresponding amides and/or carboxylic acids

  摘要：

  DOI：

  10.1021/jo00063a048

文献信息

• Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates
  作者：Juan Manuel Benito、Carmen Ortiz Mellet、José Manuel Garcı́a Fernández

  DOI：10.1016/s0008-6215(99)00273-6

  日期：1999.1

  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.
• A mild and simple enzymic conversion of aldono- and aldurononitriles into the corresponding amides and/or carboxylic acids
  作者：Anna de Raadt、Herfried Griengl、Norbert Klempier、Arnold E. Stuetz

  DOI：10.1021/jo00063a048

  日期：1993.5
• Sugar Thioureas as Anion Receptors. Effect of Intramolecular Hydrogen Bonding in the Carboxylate Binding Properties of Symmetric Sugar Thioureas
  作者：José L. Jiménez Blanco、Juan M. Benito、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/ol990889s

  日期：1999.10.1