(3'S)-5-deoxy-5-(N-hydroxyamino)-1,2-O-isopropylidene-3,N⁵-(1,1-ethano)-α-D-ribofuranose | 175877-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (3'S)-5-deoxy-5-(N-hydroxyamino)-1,2-O-isopropylidene-3,N⁵-(1,1-ethano)-α-D-ribofuranose
• 英文别名: (1R,2R,6R,8R,11S)-10-hydroxy-4,4,11-trimethyl-3,5,7-trioxa-10-azatricyclo[6.3.0.02,6]undecan-1-ol
• CAS: 175877-39-1
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: HSFVARFPPJMXEF-RZWYQDGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.39
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3'S)-5-deoxy-5-(N-hydroxyamino)-1,2-O-isopropylidene-3,N⁵-(1,1-ethano)-α-D-ribofuranose 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 生成 (3'S)-5-(N-acetoxyamino)-1,2,3-tri-O-acetyl-5-deoxy-3,N⁵-(1,1-ethano)-β-D-ribofuranose 、 (3'S)-5-(N-acetoxyamino)-1,2,3-tri-O-acetyl-5-deoxy-3,N⁵-(1,1-ethano)-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis and Conformational Analysis of A Novel Type of Spin Labelled Bicyclonucleoside Based on A Tetrahydrofurano[2,3-c]Pyrrolidine Sugar Skeleton

  摘要：

  Bicyclonucleosides bearing a 5-deoxy-5-N-hydroxyamino-3,N-5-(1,1-ethano)-beta-D-furanosyl sugar moiety (15-18) have been prepared by glycosidation of the corresponding bicyclosugars obtained via an intramolecular reverse Cope elimination. The configuration of the asymmetric carbon of the 1,1-ethano bridge is the most important factor directing the conformation of the N-hydroxypyrrolidine ring and its invertomers ratio as shown by variable temperature H NMR experiments.

  DOI：

  10.1080/07328319808004218
• 作为产物：
  描述：

  (Z)-5-deoxy-3-C-ethynyl-5-(N-hydroxyimino)-1,2-O-isopropylidene-α-D-ribofuranose 在 盐酸 、 sodium tetrahydroborate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 (3'S)-5-deoxy-5-(N-hydroxyamino)-1,2-O-isopropylidene-3,N⁵-(1,1-ethano)-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis and Conformational Analysis of A Novel Type of Spin Labelled Bicyclonucleoside Based on A Tetrahydrofurano[2,3-c]Pyrrolidine Sugar Skeleton

  摘要：

  Bicyclonucleosides bearing a 5-deoxy-5-N-hydroxyamino-3,N-5-(1,1-ethano)-beta-D-furanosyl sugar moiety (15-18) have been prepared by glycosidation of the corresponding bicyclosugars obtained via an intramolecular reverse Cope elimination. The configuration of the asymmetric carbon of the 1,1-ethano bridge is the most important factor directing the conformation of the N-hydroxypyrrolidine ring and its invertomers ratio as shown by variable temperature H NMR experiments.

  DOI：

  10.1080/07328319808004218