3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-gluco-furanose | 41545-33-9

• 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: 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-gluco-furanose
• 英文别名: 3-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropylidene-α-D-glucofuranose；3-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropyliden-α-D-glucofuranose；3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-6-nitro-α-D-glucofuranose；(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-nitroethanol
• CAS: 41545-33-9
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: ASCZPQFSJKWFJM-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-gluco-furanose 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction

  摘要：

  The Henry reaction with the easily available alpha-D-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-D-gluco- and beta-L-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-D-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-D-gluco- and beta-L-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.007
• 作为产物：
  描述：

  溴代硝基甲烷 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以75%的产率得到3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-gluco-furanose
  参考文献：
  名称：

  Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

  摘要：

  We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.

  DOI：

  10.1055/s-0031-1290441

文献信息

• One-pot synthesis of vicinal aminoalkanols from sugar aldehydes
  作者：Raquel G. Soengas、Artur M.S. Silva

  DOI：10.1016/j.tet.2013.02.072

  日期：2013.4

  A novel synthetic method of carbohydrate derived vicinal aminoalcohols, from sugar aldehydes and bromonitroalkanes, has been developed. It involves an indium-catalyzed one-pot Henry reaction and nitro group reduction, and proceeds with a remarkably high anti-selectivity. The reaction of the intermediate aminoalcohols with alkylating agents furnished the corresponding carbohydrate-based tertiary aminoalcohols

  从糖醛和溴硝基烷烃合成了一种新的碳水化合物衍生的邻氨基醇的合成方法。它涉及铟催化的一锅亨利反应和硝基还原，并以非常高的抗选择性进行。中间氨基醇与烷基化剂的反应为相应的基于碳水化合物的叔氨基醇提供了优异的立体选择性。这种非常简单的方法可以轻松地获得N，N-二烷基化邻氨基氨基链烷醇的家族，用于合成具有生物意义的衍生物和用于不对称催化的基于糖的立体分化剂的有用中间体。
• Indium-Mediated Reaction of 1-Bromo-1-nitroalkanes with Aldehydes: Access to 2-Nitroalkan-1-ols
  作者：Raquel G. Soengas、Amalia M. Estévez

  DOI：10.1002/ejoc.201000662

  日期：2010.9

  A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel

  报道了一种通过溴硝基甲烷与多种醛的铟促进反应制备 2-nitroalkan-1-ols 的新方法。该反应也用 2-溴-2-硝基丙烷进行，得到 2,2-二烷基-2-硝基烷-1-醇。手性糖衍生醛的使用为相应的 2-nitroalkan-1-ols 提供了出色的立体选择性。新的糖衍生的 2,2-二烷基-2-硝基烷-1-醇用于制备支化亚氨基糖衍生物的效用通过羟甲基支化多羟基化氮杂环庚烷的制备得到证明。
• Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium
  作者：Humberto Rodríguez-Solla、Raquel Soengas、Noemí Alvaredo

  DOI：10.1055/s-0031-1290441

  日期：2012.9

  We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.
• Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
  作者：Chaitali Chakraborty、Dilip D. Dhavale

  DOI：10.1016/j.carres.2006.02.007

  日期：2006.5

  The Henry reaction with the easily available alpha-D-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-D-gluco- and beta-L-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-D-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-D-gluco- and beta-L-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes. (c) 2006 Elsevier Ltd. All rights reserved.