1,2-O-isopropylidene-5-triisopropylsilyl-D-ribofuranose | 491580-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-triisopropylsilyl-D-ribofuranose
• CAS: 491580-13-3
• 化学式: C₁₇H₃₄O₅Si
• 分子量: 346.539
• InChiKey: BXIAODHSVAOMGV-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-triisopropylsilyl-D-ribofuranose 在 吡啶 、 sodium azide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 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：

  Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)00873-6
• 作为产物：
  描述：

  (3aR,5R,6aS)-2,2-dimethyl-5-[tri(propan-2-yl)silyloxymethyl]-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1,2-O-isopropylidene-5-triisopropylsilyl-D-ribofuranose
  参考文献：
  名称：

  Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)00873-6