1-[3-C-ethynyl-3-O-(2-propynyl)-β-D-ribo-pyranosyl]thymine | 1384102-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-C-ethynyl-3-O-(2-propynyl)-β-D-ribo-pyranosyl]thymine
• 英文别名: 1-[(2R,3R,4R,5R)-4-ethynyl-3,5-dihydroxy-4-prop-2-ynoxyoxan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1384102-13-9
• 化学式: C₁₅H₁₆N₂O₆
• 分子量: 320.302
• InChiKey: HWIOKRIEISESGX-NDPMZMCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(3aR,5R,6R,6aR)-6-ethynyl-2,2-dimethyl-6-prop-2-ynoxy-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methoxy-tert-butyl-dimethylsilane 在 甲醇 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 10.33h， 生成 1-[3-C-ethynyl-3-O-(2-propynyl)-β-D-ribo-pyranosyl]thymine
  参考文献：
  名称：

  Spiroannulated Nucleosides and Process for the Preparation Thereof

  摘要：

  我们提出了一种简单的合成策略，用于合成一系列C(3′)-螺二氢异苯并呋喃和C(3′)-螺二氢异苯并呋喃核苷，其特点是[2+2+2]-环三聚化反应作为关键反应。未保护的核苷具有二炔基团，环三聚化反应是容易进行的。当二炔基团的两个炔基都是末端时，区域选择性较差。然而，当一个末端炔基另外被取代时，环三聚化反应具有很高的立体选择性。由于关键的双环融合是最后一步，这种策略在炔烃方面提供了灵活性，因此适合用于合成一个专注的小分子库。

  公开号：

  US20130289266A1

文献信息

• Spiroannulated nucleosides and process for the preparation thereof
  申请人：Council of Scientific & Industrial Research

  公开号：US20160185811A1

  公开（公告）日：2016-06-30

  We claim a simple strategy for the synthesis of a collection of C(3′)-spirodihydroisobenzo-furannulated and C(3′)-spirodihydroisobenzo-furannulated nucleosides featuring a [2+2+2]-cyclotrimerization as the key reaction. The cyclotrimerization reactions are facile with the unprotected nucleosides having a diyne unit. When both alkynes of the diyne are terminal, the regioselectivity is poor. However, when one of the terminal alkynes is additionally substituted, the cyclotrimerizations are highly diastereoselective. Since the key bicycloannulation is the final step, this strategy provides flexibility in terms of the alkynes and is thus amenable for the synthesis of a focussed small molecule library.
• US9346847B2
  申请人：——

  公开号：US9346847B2

  公开（公告）日：2016-05-24
• Spiroannulated Nucleosides and Process for the Preparation Thereof
  申请人：Chepuri Venkata Ramana

  公开号：US20130289266A1

  公开（公告）日：2013-10-31

  We claim a simple strategy for the synthesis of a collection of C(3′)-spirodihydroisobenzo- furannulated and C(3′)-spirodihydroisobenzo-furannulated nucleosides featuring a [2+2+2]-cyclotrimerization as the key reaction. The cyclotrimerization reactions are facile with the unprotected nucleosides having a diyne unit. When both alkynes of the diyne are terminal, the regioselectivity is poor. However, when one of the terminal alkynes is additionally substituted, the cyclotrimerizations are highly diaste reoselective. Since the key bicycloannulation is the final step, this strategy provides flexibility in terms of the alkynes and is thus amenable for the synthesis of a focussed small molecule library.

  我们提出了一种简单的合成策略，用于合成一系列C(3′)-螺二氢异苯并呋喃和C(3′)-螺二氢异苯并呋喃核苷，其特点是[2+2+2]-环三聚化反应作为关键反应。未保护的核苷具有二炔基团，环三聚化反应是容易进行的。当二炔基团的两个炔基都是末端时，区域选择性较差。然而，当一个末端炔基另外被取代时，环三聚化反应具有很高的立体选择性。由于关键的双环融合是最后一步，这种策略在炔烃方面提供了灵活性，因此适合用于合成一个专注的小分子库。