1-[(2R,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-prop-2-enyloxolan-2-yl]-2-nitroethanol | 936112-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2R,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-prop-2-enyloxolan-2-yl]-2-nitroethanol
• CAS: 936112-17-3
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: SJPDZBZAPWDGPW-VZLBGKQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-prop-2-enyloxolan-2-yl]-2-nitroethanol 在 sodium tetrahydroborate 、 jones reagent 、 TEA 、 mercury(II) diacetate 、 potassium carbonate 、 甲基磺酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.5h， 生成 (1S,2S,3R,4R,6S)-1-acetylmethyl-2,3-di-O-benzyl-4-hydroxy-6-nitrocyclohexane
  参考文献：
  名称：

  Polyhydroxylated Indolines and Oxindoles from C-Glycosides via Sequential Henry Reaction, Michael Addition, and Reductive Amination/Amidation

  摘要：

  [GRAPHIC]6-Nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield.

  DOI：

  10.1021/jo070014o
• 作为产物：
  描述：

  ((2R,3R,4S,5R)-5-Allyl-3,4-bis-benzyloxy-tetrahydro-furan-2-yl)-methanol 在 三聚氯氰 、 TEA 、 sodium methylate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-[(2R,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-prop-2-enyloxolan-2-yl]-2-nitroethanol
  参考文献：
  名称：

  Polyhydroxylated Indolines and Oxindoles from C-Glycosides via Sequential Henry Reaction, Michael Addition, and Reductive Amination/Amidation

  摘要：

  [GRAPHIC]6-Nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield.

  DOI：

  10.1021/jo070014o

文献信息

• Triazole-fused sugars from nitroalkene-containing C-glycosides by a tandem 1,3-dipolar cycloaddition and intramolecular Michael addition
  作者：Wei Zou、Milan Bhasin、Kannan Vembaiyan、Dean T. Williams

  DOI：10.1016/j.carres.2009.03.007

  日期：2009.5

  A synthetic method to triazole-fused sugars by treatment of nitroalkene-containing C-glycosides with sodium azide is described. Initial experiments conducted at room temperature gave only the 1,3-dipolar cycloaddition products. However, at elevated reaction temperature the tandem beta-elimination/cycloaddition/Michael addition yielded 1,5-disubstituted triazole-fused sugars.

  描述了通过用叠氮化钠处理含硝基烯烃的C-糖苷来合成三唑融合糖的方法。在室温下进行的初始实验仅得到1，3-偶极环加成产物。然而，在升高的反应温度下，串联的β-消除/环加成/ Michael加成产生1，5-二取代的三唑稠合的糖。