3,4-dideoxy-1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-erythrohex-3-enofuranose | 1610619-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dideoxy-1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-erythrohex-3-enofuranose
• CAS: 1610619-24-3
• 化学式: C₁₃H₁₉NO₇
• 分子量: 301.296
• InChiKey: KGGKIRIAZMGWQS-FBIMIBRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  89.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitromethylene-α-D-ribo-hexofuranose 在 三乙胺 、 DL-脯氨酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3,4-dideoxy-1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-erythrohex-3-enofuranose
  参考文献：
  名称：

  Diastereoselective aza-Michael addition for synthesis of carbohydrate-derived spiropiperazinones

  摘要：

  3-Deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene--d-glucofuranose reacts with amino acid esters according to the aza-Michael addition pathway. The obtained adducts after reduction of the nitro group spontaneously lactamize and provide novel carbohydrate-derived spiropiperazinones.[GRAPHICS].

  DOI：

  10.1007/s00706-018-2304-x

文献信息

• Stereoselective Michael addition of <i>O</i>-nucleophiles to carbohydrate-based nitro-olefin
  作者：Ilgvalds Ivanovs、Santa Bērziņa、Jevgeņija Lugiņina、Sergey Belyakov、Vitālijs Rjabovs

  DOI：10.1515/hc-2016-0003

  日期：2016.4.1

  Abstract Michael addition reactions of O-nucleophiles to C(3) exocyclic nitromethylene derivative of diacetone glucose are reported. The reactions with primary alcohols proceed at ambient temperature in the presence of different bases with good yields and give products with excellent diastereoselectivity. The addition of the nucleophile occurs from the β-face of the carbohydrate as shown by single

  摘要 报道了 O-亲核试剂与双丙酮葡萄糖的 C(3) 环外硝基亚甲基衍生物的迈克尔加成反应。与伯醇的反应在环境温度下在不同碱的存在下以良好的收率进行，并得到具有优异非对映选择性的产物。如单晶 X 射线分析所示，亲核试剂的添加发生在碳水化合物的 β 面。与仲醇反应的产物产率低，而酚类化合物不反应。在某些条件下，观察到起始材料的异构化。
• Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses
  作者：Māris Turks、Krista Vēze、Gļebs Kiseļovs、Jevgeņija Mackeviča、Jevgeņija Lugiņina、Anatoly Mishnev、Dean Marković

  DOI：10.1016/j.carres.2014.03.003

  日期：2014.6

  A practical method for the synthesis of three novel 3-C-nitromethyl-hexofuranoses is reported. The Henry reaction on a 1,2: 5,6-di-O-isopropylidene-alpha-D-gulofuranose-derived ketone provided a 3-C-branched gulo-isomer as the sole reaction product. The dehydration-rehydration of the latter yielded an isopropylidene-protected 3-C-nitromethyl-galactofuranose. The reaction sequence can be also used for the synthesis of a 3-deoxy-3-C-nitromethyl-hexofuranose derivative with a gulo-configuration. Two of the newly obtained carbohydrate derivatives were characterized by X-ray crystallography. (C) 2014 Elsevier Ltd. All rights reserved.