1-[(2R,3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-4-(3-hydroxy-propyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 183987-38-4

• 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: 1-[(2R,3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-4-(3-hydroxy-propyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,4S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-4-(3-hydroxypropyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 183987-38-4
• 化学式: C₂₄H₄₆N₂O₇Si₂
• 分子量: 530.809
• InChiKey: DPRIMIQUUKHPTM-CWMLTSOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-4-(3-hydroxy-propyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到1-[(5S,6R,8R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-1,7-dioxa-spiro[4.4]non-8-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Stereoselective Preparation of 3'-C-Allyluridines and 3'-Spiro-gamma-Lactone Uridine Analogues.

  摘要：

  Grignard reactions of 3'-ketouridines 1a-c with allylmagnesium bromide and CeCl3 afforded novel 3'-C-allyluridines 2a-c and 3d-e. The diprotected 3'-keto nucleosides 1a-c afforded xylo-configurated compounds 2a-c and the 5'-unprotected 3'-keto nucleosides 1d-e afforded mixtures of xylo- and ribo-configurated compounds 2d/3d and 2e/3e. The allyluridine 2a was converted into the diol 4 by standard hydroboration and further oxidised to the 3'-spiro-gamma-lactone nucleoside 5. This compound and its deprotected analogue 6 are the first examples of a novel class of 3'-spiro nucleoside analogues.

  DOI：

  10.3891/acta.chem.scand.50-1030
• 作为产物：
  描述：

  2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine 在 sodium hydroxide 、 cerium(III) chloride 、 BH₃ in oxathiane 、 硼烷 、 双氧水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.75h， 生成 1-[(2R,3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-4-(3-hydroxy-propyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Stereoselective Preparation of 3'-C-Allyluridines and 3'-Spiro-gamma-Lactone Uridine Analogues.

  摘要：

  Grignard reactions of 3'-ketouridines 1a-c with allylmagnesium bromide and CeCl3 afforded novel 3'-C-allyluridines 2a-c and 3d-e. The diprotected 3'-keto nucleosides 1a-c afforded xylo-configurated compounds 2a-c and the 5'-unprotected 3'-keto nucleosides 1d-e afforded mixtures of xylo- and ribo-configurated compounds 2d/3d and 2e/3e. The allyluridine 2a was converted into the diol 4 by standard hydroboration and further oxidised to the 3'-spiro-gamma-lactone nucleoside 5. This compound and its deprotected analogue 6 are the first examples of a novel class of 3'-spiro nucleoside analogues.

  DOI：

  10.3891/acta.chem.scand.50-1030

文献信息

• Stereoselective Preparation of 3'-C-Allyluridines and 3'-Spiro-gamma-Lactone Uridine Analogues.
  作者：P. Nielsen、K. Larsen、J. Wengel、Neucírio Ricardo de Azevedo、Pedro Henrique Ferri、Kristian Rønning Pedersen、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-1030

  日期：——

  Grignard reactions of 3'-ketouridines 1a-c with allylmagnesium bromide and CeCl3 afforded novel 3'-C-allyluridines 2a-c and 3d-e. The diprotected 3'-keto nucleosides 1a-c afforded xylo-configurated compounds 2a-c and the 5'-unprotected 3'-keto nucleosides 1d-e afforded mixtures of xylo- and ribo-configurated compounds 2d/3d and 2e/3e. The allyluridine 2a was converted into the diol 4 by standard hydroboration and further oxidised to the 3'-spiro-gamma-lactone nucleoside 5. This compound and its deprotected analogue 6 are the first examples of a novel class of 3'-spiro nucleoside analogues.