[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-iodooxolan-2-yl]methyl benzoate | 196867-36-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-iodooxolan-2-yl]methyl benzoate
• CAS: 196867-36-4
• 化学式: C₂₃H₂₀IN₃O₆
• 分子量: 561.333
• InChiKey: ZSIGQTYYHOELNE-RSPOEFSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-iodooxolan-2-yl]methyl benzoate 在 sodium hydrogensulfide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到Benzoic acid (2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Highly efficient synthesis of 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′,3′-trans-elimination. From iodomethylcyclopropanes to thiirane analogs

  摘要：

  Taking into account the thiophilic properties of iodine, a very simple methodology to achieve 2,3'-didehydro-2'.3'-dideoxy-beta-nucleosides in high yield was performed, using mild, and inexpensive conditions. by means of the treatment of 2'-deoxy-3'.5'-dibenzoyl-2'-iodo-beta-nucleoside derivatives with NaHS. The process has shown to be highly dependent of the relative geometry between the iodine atom and the adjacent leaving group. In this way, different essays carried out with pyranose derivatives. have concluded in no reaction when the vicinal groups to eliminate do not adopt a trans-diaxial disposition. In addition, the treatment of 2-iodomethyl-cyclopropane-1,1-dicarboxylic acid diethyl ester under the same conditions softly and readily leads to the obtention of a mixture of the expected 2-allyl-malonic acid diethyl ester (as the minor product) and the thiirane derivative 2-thiiranytmethyl-malonic acid diethyl ester (as the major product). In this case, the responsible of the reaction progress are the nucleophilic properties of the sulfur atom rather than the thiophilic character of the iodine atom. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.087
• 作为产物：
  描述：

  3,5-di-O-benzoyl-D-xylofuranose 在 咪唑 、 N-碘代丁二酰亚胺 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-iodooxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols

  摘要：

  Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00332-7