1,3,5-tri-O-benzoyl-2-C-[(trimethylsilyl)ethynyl]-α-D-ribofuranose | 188413-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-tri-O-benzoyl-2-C-[(trimethylsilyl)ethynyl]-α-D-ribofuranose
• 英文别名: [(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-hydroxy-4-(2-trimethylsilylethynyl)oxolan-2-yl]methyl benzoate
• CAS: 188413-88-9
• 化学式: C₃₁H₃₀O₈Si
• 分子量: 558.66
• InChiKey: FWRDOCSCQOQLSM-SKTIGWRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,5-tri-O-benzoyl-2-C-[(trimethylsilyl)ethynyl]-α-D-ribofuranose 在 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 四氯化锡 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 2',3',5'-tri-O-benzoyl-2'-C-[(trimethylsilyl)ethynyl]uridine
  参考文献：
  名称：

  A Short, Flexible Route toward 2‘-C-Branched Ribonucleosides

  摘要：

  A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-0-benzoyl-alpha-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC drop CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the beta-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.

  DOI：

  10.1021/jo961893+
• 作为产物：
  描述：

  ALPHA-D-赤式戊呋喃糖-2-酮 1,3,5-三苯甲酸酯 、 三甲基乙炔基硅 在 正丁基锂 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以59%的产率得到1,3,5-tri-O-benzoyl-2-C-[(trimethylsilyl)ethynyl]-α-D-ribofuranose
  参考文献：
  名称：

  A Short, Flexible Route toward 2‘-C-Branched Ribonucleosides

  摘要：

  A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-0-benzoyl-alpha-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC drop CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the beta-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.

  DOI：

  10.1021/jo961893+

文献信息

• A Short, Flexible Route toward 2‘-<i>C</i>-Branched Ribonucleosides
  作者：Rogers E. Harry-O'kuru、Jennifer M. Smith、Michael S. Wolfe

  DOI：10.1021/jo961893+

  日期：1997.3.1

  A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-0-benzoyl-alpha-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC drop CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the beta-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.