(2R,3R)-1,3-dihydroxyicosan-2-yl methanesulfonate | 1122631-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2R,3R)-1,3-dihydroxyicosan-2-yl methanesulfonate
• CAS: 1122631-29-1
• 化学式: C₂₁H₄₄O₅S
• 分子量: 408.643
• InChiKey: ACBQOBFNEWKJRO-NHCUHLMSSA-N

物化性质

• 熔点：
  74.2-74.7 °C
• 沸点：
  562.5±40.0 °C(predicted)
• 密度：
  1.025±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  27.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,3-dihydroxyicosan-2-yl methanesulfonate 、 三乙基硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以98%的产率得到(5R,6R)-3,3,9,9-tetraethyl-5-heptadecyl-4,8-dioxa-3,9-disilaundecan-6-yl methanesulfonate
  参考文献：
  名称：

  α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

  摘要：

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

  DOI：

  10.1021/ol802915h
• 作为产物：
  描述：

  在 10 % Pd(OH)2/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以96%的产率得到(2R,3R)-1,3-dihydroxyicosan-2-yl methanesulfonate
  参考文献：
  名称：

  α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

  摘要：

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

  DOI：

  10.1021/ol802915h