(SP)-1,2-O-isopropylidene-3,5-O-phenoxyphosphoryl-α-D-ribofuranose | 919530-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (SP)-1,2-O-isopropylidene-3,5-O-phenoxyphosphoryl-α-D-ribofuranose
• 英文别名: (S_P)-1,2-O-isopropylidene-3,5-O-phenoxyphosphoryl-α-D-ribofuranose
• CAS: 919530-88-4
• 化学式: C₁₄H₁₇O₇P
• 分子量: 328.259
• InChiKey: JOKKSMIOEXGNNV-DJHNKFDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (SP)-1,2-O-isopropylidene-3,5-O-phenoxyphosphoryl-α-D-ribofuranose 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到(S_P,4S,5R,1'S)-4-(1'-hydroxy-2'-isopropoxyethyl)-5-hydroxy-2-oxo-2-phenoxy-1,3,2-dioxaphosphorinane
  参考文献：
  名称：

  Nucleophilic substitution at the anomeric position of 1,2-O-isopropylidenefuranose derivatives. A novel stereoselective synthesis of cyclic phosphates analogous to cAMP

  摘要：

  .1,2-O-Isopropylidenefurano se derivatives were treated with various nucleophiles in the presence of either BF3 center dot OEt2 or trimethylsilyl trifluoromethanesulfonate (TMSOTO leading to substitution products in a regio- and stereoselective manner. In particular, nucleophilic substitution of 1,2-O-isopropylidenefuranose derivatives when treated with allyltrimethylsilane was controlled by steric and electronic factors (similar to Woerpel's stereoelectronic model). On the other hand, when 1,2-O-isopropylidenefuranose derivatives were treated with trimethylsilane, in the presence of bis-O-trimethylsityl-5-iodouracil or bis-O-trimethylsilyl-thymidine, substitution products were generated in high regio- and stereo selectivities via an unusual nucleophilic substitution with opening of the furanose ring. Based on these results, a stereoselective method for the synthesis of neutral cyclic phosphates analogous to cAMP was developed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.015
• 作为产物：
  描述：

  1,2-O-异丙基-α-D-呋喃核糖 、 二氯磷酸苯酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以51%的产率得到(R_P)-1,2-O-isopropylidene-3,5-O-phenoxyphosphoryl-α-D-ribofuranose
  参考文献：
  名称：

  Nucleophilic substitution at the anomeric position of 1,2-O-isopropylidenefuranose derivatives. A novel stereoselective synthesis of cyclic phosphates analogous to cAMP

  摘要：

  .1,2-O-Isopropylidenefurano se derivatives were treated with various nucleophiles in the presence of either BF3 center dot OEt2 or trimethylsilyl trifluoromethanesulfonate (TMSOTO leading to substitution products in a regio- and stereoselective manner. In particular, nucleophilic substitution of 1,2-O-isopropylidenefuranose derivatives when treated with allyltrimethylsilane was controlled by steric and electronic factors (similar to Woerpel's stereoelectronic model). On the other hand, when 1,2-O-isopropylidenefuranose derivatives were treated with trimethylsilane, in the presence of bis-O-trimethylsityl-5-iodouracil or bis-O-trimethylsilyl-thymidine, substitution products were generated in high regio- and stereo selectivities via an unusual nucleophilic substitution with opening of the furanose ring. Based on these results, a stereoselective method for the synthesis of neutral cyclic phosphates analogous to cAMP was developed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.015