6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranurononitrile | 35920-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranurononitrile
• 英文别名: O¹,O²-isopropylidene-α-D-gluco-6-deoxy-heptofuranurononitrile；O¹,O²-Isopropyliden-α-D-gluco-6-desoxy-heptofuranurononitril；(3R)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropanenitrile
• CAS: 35920-80-0
• 化学式: C₁₀H₁₅NO₅
• 分子量: 229.233
• InChiKey: GIGAVICPRJKAOT-ANZWQOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  91.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranurononitrile 在 diborane-dimethylsulfide complex 、 三乙胺 、 三氟乙酸 、 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-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
• 作为产物：
  描述：

  6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 在 potassium cyanide 、 乙醚 、 乙醇 作用下， 生成 6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranurononitrile
  参考文献：
  名称：

  Zur darstellung der 6-desoxy-hepturons�ure

  摘要：

  DOI：

  10.1007/bf00898756

文献信息

• Grewe; Rockstroh, Chemische Berichte, 1953, vol. 86, p. 536,542
  作者：Grewe、Rockstroh

  DOI：——

  日期：——
• Zur darstellung der 6-desoxy-hepturons�ure
  作者：V. Prey、O. Szabolcs

  DOI：10.1007/bf00898756

  日期：——
• 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.