1-[3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-β-D-threo-pentopyranosyl]pyrazole | 325690-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-[3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-β-D-threo-pentopyranosyl]pyrazole
• 英文别名: [(3R,4R,5Z,6R)-4-acetyloxy-5-hydroxyimino-6-pyrazol-1-yloxan-3-yl] acetate
• CAS: 325690-41-3
• 化学式: C₁₂H₁₅N₃O₆
• 分子量: 297.268
• InChiKey: NKCCTQYKQMBHKI-JVEMUTQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-[3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-β-D-threo-pentopyranosyl]pyrazole 在 sodium tetrahydroborate 、 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以23%的产率得到1-[(Z)-2-acetoxyimino-4-O-acetyl-2,3-dideoxy-β-D-glycero-pentopyranosyl]pyrazole
  参考文献：
  名称：

  Synthesis and Properties of 1-(3,4-DI-O-Acetyl-2-Deoxy-2-Hydroxyimino-D-Threo-Pentopyranosyl)Pyrazoles

  摘要：

  3,4-Di-O-acetyl-2-deoxy-2-nitroso-alpha -D-xylo-pentopyranosyl chloride (2) reacts with pyrazole to afford 1-[3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-alpha- (3) and beta -D-threo-pentopyranosyl]pyrazole (4). The products of condensation were modified at C-2 or C-3 to give pyrazole derivatives with 3-azido-2,3-dideoxy-2-hydroxyimino-pentopyranosyl (5,7,8,9,10), 2-acetoxyimino-2,3-dideoxy-beta -D-glycero-pentopyranosyl (12,13), beta -D-lyxo- (14), beta -D-xylopentopyranosyl (15) structures and 2,3-dihydro-2-pyrazol-1-yl-6H-pyran-3-one oximes (6,11). The conformation of the sugar residue and configuration at the anomeric centre and of the hydroxyimino group were established on the basis of H-1 NMR and polarimetric data.

  DOI：

  10.1080/07328300008544149
• 作为产物：
  描述：

  吡唑 、 3,4-di-O-acetyl-2-deoxy-2-nitroso-α-D-xylopyranosyl chloride 以 乙腈 为溶剂， 反应 3.0h， 以31%的产率得到1-[3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-α-D-threo-pentopyranosyl]pyrazole
  参考文献：
  名称：

  Synthesis and Properties of 1-(3,4-DI-O-Acetyl-2-Deoxy-2-Hydroxyimino-D-Threo-Pentopyranosyl)Pyrazoles

  摘要：

  3,4-Di-O-acetyl-2-deoxy-2-nitroso-alpha -D-xylo-pentopyranosyl chloride (2) reacts with pyrazole to afford 1-[3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-alpha- (3) and beta -D-threo-pentopyranosyl]pyrazole (4). The products of condensation were modified at C-2 or C-3 to give pyrazole derivatives with 3-azido-2,3-dideoxy-2-hydroxyimino-pentopyranosyl (5,7,8,9,10), 2-acetoxyimino-2,3-dideoxy-beta -D-glycero-pentopyranosyl (12,13), beta -D-lyxo- (14), beta -D-xylopentopyranosyl (15) structures and 2,3-dihydro-2-pyrazol-1-yl-6H-pyran-3-one oximes (6,11). The conformation of the sugar residue and configuration at the anomeric centre and of the hydroxyimino group were established on the basis of H-1 NMR and polarimetric data.

  DOI：

  10.1080/07328300008544149