7-deoxy-1,2:3,4-di-O-isopropylidene-7-nitro-D-glycero-β-D-galactoheptopyranose | 124649-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 7-deoxy-1,2:3,4-di-O-isopropylidene-7-nitro-D-glycero-β-D-galactoheptopyranose
• 英文别名: (1R)-2-nitro-1-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]ethanol
• CAS: 124649-00-9
• 化学式: C₁₃H₂₁NO₈
• 分子量: 319.312
• InChiKey: QVDVRQZTLVPBOV-VFZPANTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  7-deoxy-1,2:3,4-di-O-isopropylidene-7-nitro-D-glycero-β-D-galactoheptopyranose 生成 (E)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-6-eno-1,5-pyranose
  参考文献：
  名称：

  TRONCHET, JEAN M. J.;ZERELLI, SAMI, J. CARBOHYDR. CHEM., 8,(1989) N, C. 217-232

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2：3,4-二-O-异亚丙基-α-D-半乳糖-己二醛-1,5-吡喃糖 、 硝基甲烷 生成 7-deoxy-1,2:3,4-di-O-isopropylidene-7-nitro-D-glycero-β-D-galactoheptopyranose
  参考文献：
  名称：

  TRONCHET, JEAN M. J.;ZERELLI, SAMI, J. CARBOHYDR. CHEM., 8,(1989) N, C. 217-232

  摘要：

  DOI：

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。
• Preparation of indium nitronates and their Henry reactions
  作者：Raquel G. Soengas、Rita Acúrcio、Artur M. S. Silva

  DOI：10.1039/c4ob01468e

  日期：——

  Indium nitronates were readily prepared from commercially available nitroalkanes by transmetallation of the corresponding lithium nitronates with indium salts. The Henry reaction of this indium organometallics with aldehydes afforded β-nitroalkanols in moderate to high yields. The use of chiral sugar aldehydes furnished the corresponding carbohydrate-derived β-nitroalkanols with excellent stereoselectivity

  可以通过将相应的硝酸锂锂与铟盐进行金属转移，轻松地从市售的硝基烷烃中制备硝酸铟盐。该铟有机金属与醛的亨利反应以中等至高收率提供了β-硝基链烷醇。手性糖醛的使用为相应的碳水化合物衍生的β-硝基链烷醇提供了出色的立体选择性。
• 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.