2-methyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-oxadiazole | 68115-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-oxadiazole
• 英文别名: (1R)-tri-O-benzoyl-1-(5-methyl-[1,3,4]oxadiazol-2-yl)-D-1,4-anhydro-ribitol；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(5-methyl-1,3,4-oxadiazol-2-yl)oxolan-2-yl]methyl benzoate
• CAS: 68115-92-4
• 化学式: C₂₉H₂₄N₂O₈
• 分子量: 528.518
• InChiKey: XSBROPWDUSGTRT-ZGFBMJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  127.05
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-oxadiazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以67%的产率得到2-methyl-5-(β-D-ribofuranosyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Preparation and Utility of 5-β-D-Ribofuranosyl-1H-tetrazole as a Key Synthon for C-Nucleoside Synthesis

  摘要：

  A synthesis of 5-beta-D-ribofuranosyl-1H-tetrazole (2) and 5-beta-D-ribo-furanosyl-1,3,4-oxadiazole-2(3H)-one (9) derivatives is described. Ring transformations of 2 have been investigated in an effort to establish the stability of this synthon for further use in dipolar cycloaddition reactions.

  DOI：

  10.1080/15257779408013218
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile 在 三氯化铝 、 sodium azide 、 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 2-methyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Preparation and Utility of 5-β-D-Ribofuranosyl-1H-tetrazole as a Key Synthon for C-Nucleoside Synthesis

  摘要：

  A synthesis of 5-beta-D-ribofuranosyl-1H-tetrazole (2) and 5-beta-D-ribo-furanosyl-1,3,4-oxadiazole-2(3H)-one (9) derivatives is described. Ring transformations of 2 have been investigated in an effort to establish the stability of this synthon for further use in dipolar cycloaddition reactions.

  DOI：

  10.1080/15257779408013218

文献信息

• C nucleosides II. Preparation of 2-?-d-ribofuranosylbenzothiazole, 5-?-D-ribofuranosyltetrazole, and 5-?-glycosyl-1,3,4-oxadiazole derivatives
  作者：I. Farkas、I. F. Szabo、R. Bognar、L. Sziladi

  DOI：10.1007/bf00471634

  日期：1978.7