[(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 | 157839-91-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: [(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
• CAS: 157839-91-3
• 化学式: C₁₇H₃₁O₈P
• 分子量: 394.402
• InChiKey: BMIAGVREVKOBLY-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(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 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到
  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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0~30.0 ℃ 、405.3 kPa 条件下， 反应 0.67h， 生成 [(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