1-α-D-(3',5'-O,O-tetraisopropyldisilyloxy-2'-deuteroribofuranosyl)-2-nitroimidazole | 916040-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-α-D-(3',5'-O,O-tetraisopropyldisilyloxy-2'-deuteroribofuranosyl)-2-nitroimidazole
• 英文别名: TIPDS-2'-[²H]-α-AZR
• CAS: 916040-32-9
• 化学式: C₂₀H₃₇N₃O₇Si₂
• 分子量: 488.693
• InChiKey: VSFGOWWWQZSKHC-OYCYMADXSA-N

反应信息

• 作为反应物：
  描述：

  1-α-D-(3',5'-O,O-tetraisopropyldisilyloxy-2'-deuteroribofuranosyl)-2-nitroimidazole 在 potassium fluoride 、 苯甲酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以77.7%的产率得到1-α-D-(2'-deuteroribofuranosyl)-2-nitroimidazole
  参考文献：
  名称：

  Stereospecific deuteration of α-furanosyl azomycin nucleosides: A model reaction for tritium radiolabeling

  摘要：

  Stereospecific synthesis of 1-alpha-D-(2-deuteroribofuranosyl)-2-nitroimidazole (2'-[H-2]-alpha-AZR) is reported. This, deuteration was independent of the con. guration of C-2' -OH group (arabinose or ribose) in sugar moiety of starting molecules. Slightly better yield (>37%) of the deuterated product, 6, from arabinosyl precursor in comparison to corresponding ribose precursor (29%) was obtained which may reflect better stereochemical availability of C-2' -OH in arabinose during oxidation. Crown copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.055
• 作为产物：
  描述：

  1-α-D-(3',5'-O,O-tetraisopropyldisilyloxy-2'-keto-ribofuranosyl)-2-nitroimidazole 在 吡啶 、 chromium(VI) oxide 、 乙酸酐 、 sodium borodeuteride 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 3.5h， 生成 1-α-D-(3',5'-O,O-tetraisopropyldisilyloxy-2'-deuteroribofuranosyl)-2-nitroimidazole
  参考文献：
  名称：

  Stereospecific deuteration of α-furanosyl azomycin nucleosides: A model reaction for tritium radiolabeling

  摘要：

  Stereospecific synthesis of 1-alpha-D-(2-deuteroribofuranosyl)-2-nitroimidazole (2'-[H-2]-alpha-AZR) is reported. This, deuteration was independent of the con. guration of C-2' -OH group (arabinose or ribose) in sugar moiety of starting molecules. Slightly better yield (>37%) of the deuterated product, 6, from arabinosyl precursor in comparison to corresponding ribose precursor (29%) was obtained which may reflect better stereochemical availability of C-2' -OH in arabinose during oxidation. Crown copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.055