[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl trifluoromethanesulfonate | 196868-09-4

• 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: [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl trifluoromethanesulfonate
• CAS: 196868-09-4
• 化学式: C₉H₁₂F₃N₃O₆S
• 分子量: 347.272
• InChiKey: OCUYDSUSTMNPLD-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.8
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl trifluoromethanesulfonate 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 32.25h， 生成
  参考文献：
  名称：

  New Electronic Analogs of the Sialyl Cation:  N-Functionalized 4-Acetamido-2,4-dihydroxypiperidines. Inhibition of Bacterial Sialidases

  摘要：

  DOI：

  10.1021/jo9708497
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside 在 吡啶 、 sodium azide 、 2,6-二叔丁基-4-甲基吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 58.88h， 生成 [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl trifluoromethanesulfonate
  参考文献：
  名称：

  New Electronic Analogs of the Sialyl Cation:  N-Functionalized 4-Acetamido-2,4-dihydroxypiperidines. Inhibition of Bacterial Sialidases

  摘要：

  DOI：

  10.1021/jo9708497

文献信息

• Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases
  作者：Hansjörg Streicher、Christoph Bohner

  DOI：10.1016/s0040-4020(02)00873-6

  日期：2002.9

  We have synthesized a series of cyclohexenephosphonates derived from D- and L-xylose, designed as core structures for the development of high affinity mimics of sialic acid and of the sialidase reaction transition state, Extension of our syntheses to both xylose enantiomers has given us access to two series of cyclohexenephosphonates with regioisomeric double bonds. We have demonstrated the selective functionalization of the hydroxyl groups towards introduction of a glycerol side chain mimic and immobilization via a silyl linker. The inhibitory activity of a selected set of compounds towards three bacterial sialidases has been tested and moderate activity was found. (C) 2002 Elsevier Science Ltd. All rights reserved.
• New Electronic Analogs of the Sialyl Cation:  N-Functionalized 4-Acetamido-2,4-dihydroxypiperidines. Inhibition of Bacterial Sialidases
  作者：Ian B. Parr、Benjamin A. Horenstein

  DOI：10.1021/jo9708497

  日期：1997.10.1