5'-O-[9-(3,5-dimethoxyphenyl)thioxanthyl]thymidine

• 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: 5'-O-[9-(3,5-dimethoxyphenyl)thioxanthyl]thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[9-(3,5-dimethoxyphenyl)thioxanthen-9-yl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₃₁H₃₀N₂O₇S
• 分子量: 574.654
• InChiKey: XQHDITMGCNSLLS-BXTSTYNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 5'-O-[9-(3,5-dimethoxyphenyl)thioxanthyl]thymidine
  参考文献：
  名称：

  S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides

  摘要：

  Several analogues of the 9-phenylthioxanthyl (S-pixyl) photocleavable protecting group have been synthesized, containing substituents on the 9-aryl ring and on the thioxanthyl backbone. Each analogue protected the 5'-hydroxy moiety of thymidine in good to excellent yield. The protected substrates were deprotected in 1:1 water: acetonitrile with irradiation at 300 nm, resulting in recovered thymidine in excellent yield, except for the nitro-substituted analogues which gave substantially lower yields. Substrates with 2,7-dibromo or 3-methoxy substitution on the thioxanthyl backbone were also deprotected efficiently with irradiation at 350 nm. Shorter irradiation times were observed in the less nucleophilic solvent mixture of 1:9 trifluoroethanol:acetonitrile, with no formation of secondary photooxidation products. Photodeprotection with high yields was also achieved in the absence of solvent, with no secondary photoproducts.

  DOI：

  10.1021/jo026009w

文献信息

• S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides
  作者：Michael P. Coleman、Mary K. Boyd

  DOI：10.1021/jo026009w

  日期：2002.11.1

  Several analogues of the 9-phenylthioxanthyl (S-pixyl) photocleavable protecting group have been synthesized, containing substituents on the 9-aryl ring and on the thioxanthyl backbone. Each analogue protected the 5'-hydroxy moiety of thymidine in good to excellent yield. The protected substrates were deprotected in 1:1 water: acetonitrile with irradiation at 300 nm, resulting in recovered thymidine in excellent yield, except for the nitro-substituted analogues which gave substantially lower yields. Substrates with 2,7-dibromo or 3-methoxy substitution on the thioxanthyl backbone were also deprotected efficiently with irradiation at 350 nm. Shorter irradiation times were observed in the less nucleophilic solvent mixture of 1:9 trifluoroethanol:acetonitrile, with no formation of secondary photooxidation products. Photodeprotection with high yields was also achieved in the absence of solvent, with no secondary photoproducts.