(5R)-3-p-ethoxyphenyl-5-hydroxy-5-(D-arabinotetritol-1-yl)-1-(2',3',4'-tri-O-benzoyl-β-D-ribofuranosyl)imidazolidine-2-thione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R)-3-p-ethoxyphenyl-5-hydroxy-5-(D-arabinotetritol-1-yl)-1-(2',3',4'-tri-O-benzoyl-β-D-ribofuranosyl)imidazolidine-2-thione
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[(5R)-3-(4-ethoxyphenyl)-5-hydroxy-2-sulfanylidene-5-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]imidazolidin-1-yl]oxolan-2-yl]methyl benzoate
• 化学式: C₄₁H₄₂N₂O₁₃S
• 分子量: 802.856
• InChiKey: BQIQVSRYVWQATK-FRTNTCMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  57
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  237
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  β-D-呋喃核糖基异硫氰酸三苯甲酸酯 、 1-p-ethoxyphenylamino-1-deoxy-D-fructose 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (5R)-3-p-ethoxyphenyl-5-hydroxy-5-(D-arabinotetritol-1-yl)-1-(2',3',4'-tri-O-benzoyl-β-D-ribofuranosyl)imidazolidine-2-thione 、 (5S)-3-p-ethoxyphenyl-5-hydroxy-5-(D-arabinotetritol-1-yl)-1-(2',3',4'-tri-O-benzoyl-β-D-ribofuranosyl)imidazolidine-2-thione
  参考文献：
  名称：

  Chiral thioxohydroimidazoles with two sugar moieties. N-, C-, and spiro-nucleosides

  摘要：

  2-Amino (alkyl and arylamino)-2-deoxy-D-fructose and different sugar isothiocyanates are used in the diastereoselective synthesis of chiral imidazolidine-2-thione hi-nucleosides 12-23. Water beta-elimination of these compounds produces imidazoline-2-thione N-nucleosides 27-31, whereas cyclodehydration of the same products gives, with high stereoselectivity, chiral spironucleosides with an N-glycosyl radical 34-37. Conformational aspects of some of the prepared compounds are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00550-9

文献信息

• Chiral thioxohydroimidazoles with two sugar moieties. N-, C-, and spiro-nucleosides
  作者：Consolación Gasch、M.Angeles Pradera、Bader A.B Salameh、José L Molina、José Fuentes

  DOI：10.1016/s0957-4166(99)00550-9

  日期：2000.2

  2-Amino (alkyl and arylamino)-2-deoxy-D-fructose and different sugar isothiocyanates are used in the diastereoselective synthesis of chiral imidazolidine-2-thione hi-nucleosides 12-23. Water beta-elimination of these compounds produces imidazoline-2-thione N-nucleosides 27-31, whereas cyclodehydration of the same products gives, with high stereoselectivity, chiral spironucleosides with an N-glycosyl radical 34-37. Conformational aspects of some of the prepared compounds are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.