1-C-allyl 2,3-di-O-benzyl-5-aldo-α-D-ribofuranoside | 936112-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-allyl 2,3-di-O-benzyl-5-aldo-α-D-ribofuranoside
• 英文别名: (2S,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-prop-2-enyloxolane-2-carbaldehyde
• CAS: 936112-16-2
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: DPKJROGEJZZXKR-YUMYIRISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-C-allyl 2,3-di-O-benzyl-5-aldo-α-D-ribofuranoside 在 sodium tetrahydroborate 、 jones reagent 、 TEA 、 mercury(II) diacetate 、 sodium methylate 、 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 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-C-allyl 2,3-di-O-benzyl-5-aldo-α-D-ribofuranoside
  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

• Polyhydroxylated Indolines and Oxindoles from <i>C</i>-Glycosides via Sequential Henry Reaction, Michael Addition, and Reductive Amination/Amidation
  作者：Wei Zou、An-Tai Wu、Milan Bhasin、Mahendra Sandbhor、Shih-Hsiung Wu

  DOI：10.1021/jo070014o

  日期：2007.3.1

  [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.