1-(5-O-benzoyl-2,3-dideoxy-α-D-glycero-pentofuranosyl)uracil | 132619-89-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(5-O-benzoyl-2,3-dideoxy-α-D-glycero-pentofuranosyl)uracil
• 英文别名: [(2S,5S)-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 132619-89-7
• 化学式: C₁₆H₁₆N₂O₅
• 分子量: 316.313
• InChiKey: PBFATPYEUBCWJS-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-5-(benzoyloxymethyl)tetrahydrofuran-2-one 在 吡啶 、 氯化亚砜 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 8.0h， 生成 1-(5-O-benzoyl-2,3-dideoxy-α-D-glycero-pentofuranosyl)uracil
  参考文献：
  名称：

  Stereoselectivities in the Coupling Reaction between Silylated Pyrimidine Bases and 1-Halo-2,3-dideoxyribose

  摘要：

  Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of alpha:beta = 4:6. On the other hand, the presence of tertiary amine raises the selectivity to alpha:beta = 3:7.

  DOI：

  10.3987/com-90-5563

文献信息

• Efficient synthesis of 2′,3′-dideoxynucleosides and 2′,3′-dideoxy C-nucleosides from D-glucosamine
  作者：Michael E. Jung、Ivan D. Trifunovich

  DOI：10.1016/s0040-4039(00)79561-x

  日期：1992.5

  D-Glucosamine 1 can be easily converted into 2,5-anhydro-6-O-benzoyl-3,4-dideoxygluconic acid 6 which can be taken on to both 2′,3′-dideoxynucleosides such as dideoxyuridine (ddU) 4 and 2′,3′-dideoxy C-nucleosides such as dideoxyformycin B 5 and dideoxyshowdomycin 20.

  D-葡糖胺1可以轻松转化为2,5-脱水-6- O-苯甲酰基-3,4-二脱氧葡萄糖酸6，可以同时用于2'，3'-二脱氧核苷，例如双脱氧尿苷（ddU）4和2'，3'-二脱氧C-核苷，例如双脱氧福霉素B 5和双脱氧showdomycin 20。
• Analogs of pyrimidine nucleosides. 16. Racemic 2?,3?-dideoxynucleosides and their derivatives
  作者：L. T. Kaulinya、�. �. Liepin'sh、M. Yu. Lidak、R. A. Zhuk

  DOI：10.1007/bf00513297

  日期：1982.1
• KAWAKAMI, HIROSHI;EBATA, TAKASHI;KOSEKI, KOSHI;MATSUMOTO, KATSUYA;MATSUSH+, HETEROCYCLES, 31,(1990) N1, C. 2041-2054
  作者：KAWAKAMI, HIROSHI、EBATA, TAKASHI、KOSEKI, KOSHI、MATSUMOTO, KATSUYA、MATSUSH+

  DOI：——

  日期：——
• Stereoselectivities in the Coupling Reaction between Silylated Pyrimidine Bases and 1-Halo-2,3-dideoxyribose
  作者：Hiroshi Kawakami、Takashi Ebata、Koshi Koseki、Katsuya Matsumoto、Hajime Matsushita、Yoshitake Naoi、Kazuo Itoh

  DOI：10.3987/com-90-5563

  日期：——

  Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of alpha:beta = 4:6. On the other hand, the presence of tertiary amine raises the selectivity to alpha:beta = 3:7.