3-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-D-ribofuranose | 459839-20-4

• 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-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: [(3aR,5S,6S,6aR)-5-(iodomethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 459839-20-4
• 化学式: C₁₅H₁₇IO₅
• 分子量: 404.201
• InChiKey: RIIYEYMIAFFECV-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-D-ribofuranose 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以82%的产率得到3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-erythro-pent-4-enofuranose
  参考文献：
  名称：

  Synthesis of nucleosides from 4-methylidenefuranoses: a non-classical electrophilic addition

  摘要：

  The reaction of persilylated bases (thymine, uracil, cytosine, and 5-fluorouracil) with either 3-O-benzoyl-5-deoxy-1,2-O- isopropylidene-alpha-D-erythro-pent-4-enofuranose 6 or its 3-O-benzyl analogue 7 in the presence of N-iodosuccinimide (NIS) afforded two types of product with high stereoselectivity: either (1's,2'R,3'S)-3'-O-benzoyl-8-10 or -3'-O-benzyl-5'-deoxy-5'-iodo-1',2'-O-isopropylidene-4'-oxo-1'-yl-pyrimidines 11-13, respectively, from 1,4-addition with participation of the oxygen atom at the furanoid ring, and either 3'-O-benzoyl- 14-16, or 3'-O-benzyl-5'-deoxy-5'-iodo-1',2'-O-isopropylidene-beta-L-lyxo-4'-yl-pyrimidine and 17-19 resulting from normal electrophilic addition at the exocyclic methylene group. A third compound was isolated from the reaction of 7 with persilylated uracil/NIS and identified as the doubly N,N'-glycosylated pyrimidine 20. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00125-8
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 咪唑 、 sodium tetrahydroborate 、 4 A molecular sieve 、 碘 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 3-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of nucleosides from 4-methylidenefuranoses: a non-classical electrophilic addition

  摘要：

  The reaction of persilylated bases (thymine, uracil, cytosine, and 5-fluorouracil) with either 3-O-benzoyl-5-deoxy-1,2-O- isopropylidene-alpha-D-erythro-pent-4-enofuranose 6 or its 3-O-benzyl analogue 7 in the presence of N-iodosuccinimide (NIS) afforded two types of product with high stereoselectivity: either (1's,2'R,3'S)-3'-O-benzoyl-8-10 or -3'-O-benzyl-5'-deoxy-5'-iodo-1',2'-O-isopropylidene-4'-oxo-1'-yl-pyrimidines 11-13, respectively, from 1,4-addition with participation of the oxygen atom at the furanoid ring, and either 3'-O-benzoyl- 14-16, or 3'-O-benzyl-5'-deoxy-5'-iodo-1',2'-O-isopropylidene-beta-L-lyxo-4'-yl-pyrimidine and 17-19 resulting from normal electrophilic addition at the exocyclic methylene group. A third compound was isolated from the reaction of 7 with persilylated uracil/NIS and identified as the doubly N,N'-glycosylated pyrimidine 20. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00125-8