1-<2'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon | 68753-36-6

• 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'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon
• 英文别名: 3',5'-p-toluoyl-β-2'-deoxyzebularine；1-[O³,O⁵-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-1H-pyrimidin-2-one；[(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-(2-oxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 68753-36-6
• 化学式: C₂₅H₂₄N₂O₆
• 分子量: 448.475
• InChiKey: SZACRDUQCRFOOQ-BHDDXSALSA-N

物化性质

• 沸点：
  608.2±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

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'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon 在 四氯化锡 、 2-[(三甲基硅烷基)氧基]嘧啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以0.15 g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：

  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：

  methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 、 2-[(三甲基硅烷基)氧基]嘧啶 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以30%的产率得到1-<2'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon
  参考文献：
  名称：

  核苷和核苷酸。Teil 22.合成烯类十三烷十二烷基磷酸酯，未知碱基2（1 H）-嘧啶酮†

  摘要：

  核苷和核苷酸。第22部分。包含非天然碱2（1 H）-嘧啶酮的十三碳十二烷基核苷十二磷酸的合成

  DOI：

  10.1002/hlca.19850680221

文献信息

• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET PROCÉDÉS ASSOCIÉS
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2022099159A1

  公开（公告）日：2022-05-12

  Among other things, the present disclosure provides oligonucleotides and compositions thereof. In some embodiments, provided oligonucleotides and compositions are useful for adenosine modification. In some embodiments, the present disclosure provides methods for treating various conditions, disorders or diseases that can benefit from adenosine modification.

  除其他事项外，本公开提供寡核苷酸及其组合物。在某些实施例中，提供的寡核苷酸及其组合物对腺苷修饰有用。在某些实施例中，本公开提供了治疗各种需要腺苷修饰的疾病、疾病或病症的方法。
• OLIGONUCLEOTIDE COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Wave Life Sciences Ltd.

  公开号：EP4022059A1

  公开（公告）日：2022-07-06
• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2021071858A1

  公开（公告）日：2021-04-15

  Among other things, the present disclosure provides oligonucleotides and compositions thereof. In some embodiments, provided oligonucleotides and compositions are useful for adenosine modification. In some embodiments, the present disclosure provides methods for treating various conditions, disorders or diseases that can benefit from adenosine modification.