Toluene-4-sulfonic acid (4R,5R)-5-[(R)-(diethoxy-phosphorylmethoxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 157839-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (4R,5R)-5-[(R)-(diethoxy-phosphorylmethoxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS: 157839-90-2
• 化学式: C₂₄H₃₉O₁₁PS
• 分子量: 566.607
• InChiKey: SJFJGQGJZUCRMO-GXRSIYKFSA-N

物化性质

• 沸点：
  645.8±55.0 °C(predicted)
• 密度：
  1.216±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  125.05
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (4R,5R)-5-[(R)-(diethoxy-phosphorylmethoxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到[(3aR,4R,6R,7aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of novel phosphonate analogue of Kdo as a tool for the design of potent inhibitors for lipopolysaccharide biosynthesis

  摘要：

  The new phosphonate analogue 3 of 2-deoxy-beta-Kdo (2) was prepared in a stereospecific manner via intramolecular C-C bond formation. X-Ray structure analysis and NMR studies of the cyclyzation product established the twist-boat conformation of the pyranose ring with alpha-anomeric configuration of the phosphonate linkage.

  DOI：

  10.1016/s0040-4039(00)73325-9
• 作为产物：
  描述：

  2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 30.0 ℃ 、405.3 kPa 条件下， 反应 0.67h， 生成 Toluene-4-sulfonic acid (4R,5R)-5-[(R)-(diethoxy-phosphorylmethoxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of novel phosphonate analogue of Kdo as a tool for the design of potent inhibitors for lipopolysaccharide biosynthesis

  摘要：

  The new phosphonate analogue 3 of 2-deoxy-beta-Kdo (2) was prepared in a stereospecific manner via intramolecular C-C bond formation. X-Ray structure analysis and NMR studies of the cyclyzation product established the twist-boat conformation of the pyranose ring with alpha-anomeric configuration of the phosphonate linkage.

  DOI：

  10.1016/s0040-4039(00)73325-9