5-O-benzoyl-3-O-carbamoyl-3-C-cyano-1,2-O-isopropylidene-α-D-ribofuranose | 250588-66-0

• 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-3-O-carbamoyl-3-C-cyano-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: [(3aR,5R,6R,6aR)-6-carbamoyloxy-6-cyano-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 250588-66-0
• 化学式: C₁₇H₁₈N₂O₇
• 分子量: 362.339
• InChiKey: OAQPIVJEIZHBQJ-DMVWFOPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-3-O-carbamoyl-3-C-cyano-1,2-O-isopropylidene-α-D-ribofuranose 在 碳酸氢钠 作用下， 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
• 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 以 水 为溶剂， 生成 5-O-benzoyl-3-O-carbamoyl-3-C-cyano-1,2-O-isopropylidene-α-D-ribofuranose
  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