1-C-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)propan-2-one ethylene ketal | 1355214-19-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-C-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)propan-2-one ethylene ketal
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-[(2-methyl-1,3-dioxolan-2-yl)methyl]oxan-2-yl]methyl acetate
• CAS: 1355214-19-5
• 化学式: C₁₉H₂₈O₁₁
• 分子量: 432.425
• InChiKey: HRKFQTSZXMFAJW-FLXSYLCISA-N

物化性质

• 沸点：
  477.7±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-C-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)propan-2-one ethylene ketal 在 甲醇 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 水 、 氢气 、 sodium 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 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：

  4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose 在 吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 1-C-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)propan-2-one ethylene ketal
  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