2-(1-C-β-D-galactopyranosylmethyl)propene | 1355214-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-C-β-D-galactopyranosylmethyl)propene
• 英文别名: (2R,3R,4R,5R,6S)-2-(hydroxymethyl)-6-(2-methylprop-2-enyl)oxane-3,4,5-triol
• CAS: 1355214-22-0
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: YKUXLYIXOZNUQW-CVPUBMOQSA-N

物化性质

• 沸点：
  391.6±42.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-C-β-D-galactopyranosylmethyl)propene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以9.9 g的产率得到1-isobutyl-β-D-galactose
  参考文献：
  名称：

  Multigram Synthesis of Isobutyl-β-C-galactoside as a Substitute of Isopropylthiogalactoside for Exogenous Gene Induction in Mammalian Cells

  摘要：

  Herein we report that isobutyl-beta-C-galactoside (IBCG) is also a promising inducer of gene expression in mammalian cells and report a new synthetic route to the compound that should make obtaining the multigram quantities of material required for animal studies more feasible. A convenient synthesis of IBCG, an inducer of genes controlled by the lac operon system in bacterial cells, was achieved in 5 steps from galactose in 81% overall yield without any chromatographic separation steps. An optimized microwave-assisted reaction at high concentration was key to making the C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.

  DOI：

  10.1021/jo2024569
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 potassium tert-butylate 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.92h， 生成 2-(1-C-β-D-galactopyranosylmethyl)propene
  参考文献：
  名称：

  Multigram Synthesis of Isobutyl-β-C-galactoside as a Substitute of Isopropylthiogalactoside for Exogenous Gene Induction in Mammalian Cells

  摘要：

  Herein we report that isobutyl-beta-C-galactoside (IBCG) is also a promising inducer of gene expression in mammalian cells and report a new synthetic route to the compound that should make obtaining the multigram quantities of material required for animal studies more feasible. A convenient synthesis of IBCG, an inducer of genes controlled by the lac operon system in bacterial cells, was achieved in 5 steps from galactose in 81% overall yield without any chromatographic separation steps. An optimized microwave-assisted reaction at high concentration was key to making the C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.

  DOI：

  10.1021/jo2024569

文献信息

• Multigram Synthesis of Isobutyl-β-<i>C</i>-galactoside as a Substitute of Isopropylthiogalactoside for Exogenous Gene Induction in Mammalian Cells
  作者：Lin Liu、Basma Abdel Motaal、Marc Schmidt-Supprian、Nicola L. B. Pohl

  DOI：10.1021/jo2024569

  日期：2012.2.3

  Herein we report that isobutyl-beta-C-galactoside (IBCG) is also a promising inducer of gene expression in mammalian cells and report a new synthetic route to the compound that should make obtaining the multigram quantities of material required for animal studies more feasible. A convenient synthesis of IBCG, an inducer of genes controlled by the lac operon system in bacterial cells, was achieved in 5 steps from galactose in 81% overall yield without any chromatographic separation steps. An optimized microwave-assisted reaction at high concentration was key to making the C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.