(5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose)-3-spiro-5'-(4'-amino-2'-oxazolone) | 250588-65-9

• 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: (5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose)-3-spiro-5'-(4'-amino-2'-oxazolone)
• 英文别名: [(3'aR,5R,5'R,6'aR)-4-amino-2',2'-dimethyl-2-oxospiro[1,3-oxazole-5,6'-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole]-5'-yl]methyl benzoate
• CAS: 250588-65-9
• 化学式: C₁₇H₁₈N₂O₇
• 分子量: 362.339
• InChiKey: AMGQEMQSGSQIKK-WYFUGZQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose)-3-spiro-5'-(4'-amino-2'-oxazolone) 、 碘甲烷 在 potassium carbonate 作用下， 生成 (5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose)-3-spiro-5'-(4'-N-methylamino-2-oxazolone) 、 [(3'aR,5R,5'R,6'aR)-4-imino-2',2',3-trimethyl-2-oxospiro[1,3-oxazolidine-5,6'-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole]-5'-yl]methyl benzoate
  参考文献：
  名称：

  Steric and Electronic Properties of the 3′-spiro Moiety of TSAO-T and Analogues

  摘要：

  The synthesis and study of geometrical and stereoelectronic properties of the spiro moiety of tof novel TSAO analogues modified at the 3'-spiro moiety is described.

  DOI：

  10.1080/15257779908041661
• 作为产物：
  描述：

  Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose)-3-spiro-5'-(4'-amino-2'-oxazolone)
  参考文献：
  名称：

  Synthesis, NMR studies and theoretical calculations of novel 3-spiro-branched ribofuranoses

  摘要：

  Novel spiro-branched sugar derivatives bearing a spiro-5'-(4'-amino-2'-oxazolone) or a spiro-5'-(4'amino-1',2',3'-oxathiazole-2',2'-dioxide) rings at position-3 of the sugar moiety have been prepared. The synthesis has been achieved by a one-pot procedure from a conveniently protected sugar cyanohydrin derivative by reaction with chlorosulfonyl isocyanate or sulfamoyl chloride, respectively. The tautomeric preference in solution of these novel 3-spiro sugars are described as derived from NMR spectroscopy. Also a comparative theoretical study, by ab-initio methods, of the steric and electronic properties of the spiro rings present in these sugar derivatives has been performed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00696-1

文献信息

• Synthesis, NMR studies and theoretical calculations of novel 3-spiro-branched ribofuranoses
  作者：María-José Camarasa、María-Luisa Jimeno、María-Jesús Pérez-Pérez、Rosa Alvarez、Sonsoles Velázquez、Angel Lozano

  DOI：10.1016/s0040-4020(99)00696-1

  日期：1999.10

  Novel spiro-branched sugar derivatives bearing a spiro-5'-(4'-amino-2'-oxazolone) or a spiro-5'-(4'amino-1',2',3'-oxathiazole-2',2'-dioxide) rings at position-3 of the sugar moiety have been prepared. The synthesis has been achieved by a one-pot procedure from a conveniently protected sugar cyanohydrin derivative by reaction with chlorosulfonyl isocyanate or sulfamoyl chloride, respectively. The tautomeric preference in solution of these novel 3-spiro sugars are described as derived from NMR spectroscopy. Also a comparative theoretical study, by ab-initio methods, of the steric and electronic properties of the spiro rings present in these sugar derivatives has been performed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Steric and Electronic Properties of the 3′-spiro Moiety of TSAO-T and Analogues
  作者：M. J. Pérez-Pérez、R. Alvarez、M. L. Jimeno、A. San-Félix、A. Lozano、M. J. Camarasa

  DOI：10.1080/15257779908041661

  日期：1999.4

  The synthesis and study of geometrical and stereoelectronic properties of the spiro moiety of tof novel TSAO analogues modified at the 3'-spiro moiety is described.