(2'R)-<2'-2H>thymidine | 108967-35-7

• 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: (2'R)-<2'-2H>thymidine
• 英文别名: 1-[(2R,3R,4S,5R)-3-deuterio-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 108967-35-7
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 243.224
• InChiKey: IQFYYKKMVGJFEH-FHOJYAAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-deoxy-2(R)-deuterio-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 在 氨 作用下， 以 甲醇 为溶剂， 生成 (2'R)-<2'-2H>thymidine
  参考文献：
  名称：

  2'-deoxy-2'（氘）和2'-deoxy-2'（r）-氘-β-d-核苷的合成

  摘要：

  氘化锂铝（LAD）促进了适当保护的甲基2,3-脱水-α-D-呋喃呋喃糖苷和甲基2,3-脱水-β-D-呋喃呋喃糖苷的开环反应，得到2-脱氧-2（）-氘-戊糖和2-deoxy-2（）--戊糖衍生物和。化合物和随后转化为2-脱氧-2（S）-deuterio-和2-脱氧-2（）-deuterio- -pentofuranosyl氯化物，和respectively.Thymine，胞嘧啶，6-氯嘌呤和2-氨基-6-氯嘌呤然后用这些α-chlorosugars糖基化，并且，得到相应的立体有择性标记的2-脱氧-2（）-deuterio-和2-脱氧-2（）-氘-β-D-核苷

  DOI：

  10.1016/s0040-4020(01)82094-9

文献信息

• Sonochemical and triethylborane-induced tin deuteride reduction for the highly stereoselective synthesis of (2′R)-[2′-2H]-2′-deoxyribonucleosides from 2′-functionalized ribonucleosides
  作者：Etsuko Kawashima、Yukio Aoyama、Takeshi Sekine、Eiichi Nakamura、Masatsune Kainosho、Yoshimasa Kyogoku、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(00)91784-2

  日期：1993.2

  (Bu3SnH)-H-2-reduction of a 2'-bromo-2'-deoxyuridine benzoate under high-intensity ultrasound irradiation at -71-degrees-C resulted in highly efficient deuterium incorporation to afford a 96:4 mixture of (2'R)- and (2'S)-[2,-H-2]-2'-deoxyuridine. The use of both Et3B, as an alternative radical generator, and 2'-bromo-2'-deoxy-3',5'-O-TPDS-ribonucleosides made it feasible to perform the reaction in a preparative scale in addition to an excellent stereoselectivity (>99:1).

  在-71摄氏度下，通过高强度超声波辐照，(Bu3SnH)对2'-溴-2'-脱氧尿苷苯甲酸酯进行H-2还原，成功实现了高效氘掺入，生成了(2'R)-和(2'S)-[2,-H-2]-2'-脱氧尿苷的96:4混合物。同时，使用乙基三甲基锡（Et3B）作为替代的自由基生成剂，以及2'-溴-2'-脱氧-3',5'-O-TPDS-核糖核苷作为反应物，使得该反应不仅能在制备规模上进行，而且还具有极高的立体选择性（>99:1）。
• Sonochemical and Triethylborane-Induced Tin Deuteride Reduction for the Highly Diastereoselective Synthesis of (2'R)-2'-Deoxy[2'-2H]ribonucleoside Derivatives
  作者：Etsuko Kawashima、Yukio Aoyama、Takeshi Sekine、Masayoshi Miyahara、Mohamed F. Radwan、Eiichi Nakamura、Masatsune Kainosho、Yoshimasa Kyogoku、Yoshiharu Ishido

  DOI：10.1021/jo00126a058

  日期：1995.10

  For the NMR spectroscopic conformational analysis of a sugar moiety in a DNA complex with a protein or a drug, (2'R)- and/or (2'S)-2'-deoxy[2'-H-2]ribonucleoside derivatives with high purity are useful. To develop a highly diastereoselective and efficient method for the synthesis of(2'R)-2'-deoxy[2'-H-2]ribonucleoside derivatives, studies of leaving groups (OPTC, Br) at the 2' position of nucleosides, of the effects of reaction temperature on diastereoselectivity, of radical generation (ultrasound irradiation, Et(3)B) at temperatures as low as -70 degrees C, and of protecting groups for the 3' and 5' hydroxyl groups (benzoate, TPDS) of nucleosides were carried out. Bu(3)Sn(2)H-reductive deuteration of 3',5'-di-0-benzoyl-2'-bromo-2'-deoxyuridine under high-intensity ultrasound irradiation at -71 degrees C induced notably efficient deuterium incorporation to afford a highly diastereoselective 3',5'-di-0-benzoyl-2'-deoxy[2'-H-2]uridin [(2'R):(2'S) = 96:4]. The use of Et(3)B, as an alternative radical generator, toward 2'-bromo-2'-deoxy-3',5'-0-TPDS-ribonucleosides at <--70 degrees C made it feasible to perform the reaction on a preparative scale, and provided excellent diastereoselectivity (2'-deoxyadenosine, thymidine, and 2'-deoxyuridine derivatives >99:1 which were converted to (2'R)-2'-deoxy[2'-H-2]cytidine derivatives, guanosine derivative = 91:9).