3-O-benzyl-1,2-O-isopropylidene-α-L-ribofuranose | 679394-50-4

• 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: 3-O-benzyl-1,2-O-isopropylidene-α-L-ribofuranose
• 英文别名: [(3aS,5S,6S,6aS)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• CAS: 679394-50-4
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ACGQAKYHAOEVJI-XUXIUFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-L-ribofuranose 在 2,6-二甲基吡啶 、 15-冠醚-5 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 tetramethyl (3-O-benzyl-1,2-O-isopropylidene-3,5,6-trideoxy-α-L-ribofuranose-6,6'-diyl)bisphosphonate
  参考文献：
  名称：

  Galactose‐Phosphonates as Mimetics of the Sialyltransfer by Trypanosomal Sialidases

  摘要：

  In an attempt to find competitive inhibitors of the trans- sialidase of the pathogen Trypanosoma cruzi, we have synthesized conjugates of carbocyclic sialylmimetics ( e. g., cyclohexenephosphonates) and galactose derivatives. A trans- sialidase inhibition assay revealed an interesting preference for ethylidene- spacered conjugates involving the 3- position of the sugar.

  DOI：

  10.1080/07328300701351532
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-α-L-ribofuranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到3-O-benzyl-1,2-O-isopropylidene-α-L-ribofuranose
  参考文献：
  名称：

  Galactose‐Phosphonates as Mimetics of the Sialyltransfer by Trypanosomal Sialidases

  摘要：

  In an attempt to find competitive inhibitors of the trans- sialidase of the pathogen Trypanosoma cruzi, we have synthesized conjugates of carbocyclic sialylmimetics ( e. g., cyclohexenephosphonates) and galactose derivatives. A trans- sialidase inhibition assay revealed an interesting preference for ethylidene- spacered conjugates involving the 3- position of the sugar.

  DOI：

  10.1080/07328300701351532

文献信息

• A novel synthesis of deoxy phospha sugar–sugar disaccharides
  作者：Buchammagari Haritha、Valluru Krishna Reddy、Tatsuo Oshikawa、Mitsuji Yamashita

  DOI：10.1016/j.tetlet.2003.12.134

  日期：2004.2

  A novel and facile synthetic method is described in the synthesis of several deoxy phospha sugar–sugar disaccharides, analogs of normal sugar disaccharides by treatment of (±)-2-bromo-3-methoxy-1-phenylphospholane 1-oxide with several pentose and hexose sugar acetonides.

  一种新颖且简便的合成方法描述于几种脱氧磷酸糖-糖二糖的合成中，这是通过用几种戊糖和（-）-2-溴-3--3-甲氧基-1-苯基正膦1氧化物处理正糖二糖的类似物。己糖丙酮化物。
• Galactose‐Phosphonates as Mimetics of the Sialyltransfer by Trypanosomal Sialidases
  作者：Heike Busse、Mitsuru Hakoda、Matthew Stanley、Hansjörg Streicher

  DOI：10.1080/07328300701351532

  日期：2007.5.31

  In an attempt to find competitive inhibitors of the trans- sialidase of the pathogen Trypanosoma cruzi, we have synthesized conjugates of carbocyclic sialylmimetics ( e. g., cyclohexenephosphonates) and galactose derivatives. A trans- sialidase inhibition assay revealed an interesting preference for ethylidene- spacered conjugates involving the 3- position of the sugar.