1-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-2(1H)-pyrimidinone | 68753-37-7

• 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-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-2(1H)-pyrimidinone
• 英文别名: 3',5'-p-toluoyl-α-2'-deoxyzebularine；1-[O³,O⁵-bis-(4-methyl-benzoyl)-α-D-erythro-2-deoxy-pentofuranosyl]-1H-pyrimidin-2-one；[(2R,3S,5S)-3-(4-methylbenzoyl)oxy-5-(2-oxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 68753-37-7
• 化学式: C₂₅H₂₄N₂O₆
• 分子量: 448.475
• InChiKey: SZACRDUQCRFOOQ-BDTNDASRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.72
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-2(1H)-pyrimidinone 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以91%的产率得到1-(2'-deoxy-α-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone
  参考文献：
  名称：

  Efficient synthesis of 2′-deoxyzebularine and its α-anomer by the silyl method of N-glycosylation. Crystal structures and conformational study in solution

  摘要：

  2'-Deoxyzebularine and its alpha-anomer have been efficiently synthesized with relatively high stereoselectivity by a modified procedure of the silyl method of the N-glycosidic bond formation. An SnCl4-catalyzed condensation of silylated pyrimidin-2-one with 1-alpha-chloro-3,5-di-O-p-toluoy1-2-deoxy-D-ribofuranose under kinetic control condition (-33 degrees C, 1,2-dichloroethane) led to the mixture of beta- and alpha-anomeric nucleosides in 3:1 ratio. Analogous condensation at +35 degrees C (thermodynamic control conditions) provided mainly p-toluoyl protected alpha-2'-deoxyzebularine (alpha:beta= 4:1), easily separated by crystallization from the anomeric mixture. The structures of both 2'-deoxyzebularine anomers were confirmed by X-ray analysis of the crystals and conformational studies in solution performed using an NMR method. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.03.018
• 作为产物：
  描述：

  2-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyloxy>pyrimidine 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以84%的产率得到1-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-2(1H)-pyrimidinone
  参考文献：
  名称：

  Seela, Frank; Bindig, Uwe, Liebigs Annalen der Chemie, 1989, p. 895 - 902

  摘要：

  DOI：

文献信息

• SEELA, FRANK;BINDIG, UWE, LIEBIGS ANN. CHEM.,(1989) N, C. 895-901
  作者：SEELA, FRANK、BINDIG, UWE

  DOI：——

  日期：——