(R)-sulfoxide of 2'-deoxy-4'-deuterio-5-ethyl-4'-thio-β-D-uridine | 214688-82-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (R)-sulfoxide of 2'-deoxy-4'-deuterio-5-ethyl-4'-thio-β-D-uridine
• CAS: 214688-82-1
• 化学式: C₁₁H₁₆N₂O₅S
• 分子量: 289.317
• InChiKey: CPBAMSGUCROIBU-RVTFDBOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  112.39
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-sulfoxide of 2'-deoxy-4'-deuterio-5-ethyl-4'-thio-β-D-uridine 在 三甲基溴硅烷 、 三氟乙酸 作用下， 反应 0.33h， 以54%的产率得到2'-deoxy-4'-deuterio-5-ethyl-4'-thio-β-D-uridine
  参考文献：
  名称：

  A novel method for deuteration of 2′-deoxy-4′-thionucleosides

  摘要：

  Oxidation of 2'-deoxy-5-ethyl-4'-thiouridine with sodium meta-periodate yielded a separable mixture of (R) and(S)-sulfoxides. The structure of the (R)-sulfoxide was confirmed by X-ray analysis. When treated with sodium deuteroxide, the H-4' proton was exchanged for deuterium with epimerisation at C-4'. Treatment of the deuteriated sulfoxide nucleoside with TFA/TMSBr furnished the starting material with H-4' replaced by deuterium. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00727-3
• 作为产物：
  描述：

  4'-硫代-5-乙基-2'-脱氧尿苷 在 sodium periodate 、 氘氧化钠 作用下， 以 甲醇 、 水 、 重水 为溶剂， 反应 18.0h， 生成 (R)-sulfoxide of 2'-deoxy-4'-deuterio-5-ethyl-4'-thio-β-D-uridine
  参考文献：
  名称：

  A novel method for deuteration of 2′-deoxy-4′-thionucleosides

  摘要：

  Oxidation of 2'-deoxy-5-ethyl-4'-thiouridine with sodium meta-periodate yielded a separable mixture of (R) and(S)-sulfoxides. The structure of the (R)-sulfoxide was confirmed by X-ray analysis. When treated with sodium deuteroxide, the H-4' proton was exchanged for deuterium with epimerisation at C-4'. Treatment of the deuteriated sulfoxide nucleoside with TFA/TMSBr furnished the starting material with H-4' replaced by deuterium. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00727-3