9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine | 622379-64-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine
• CAS: 622379-64-0
• 化学式: C₃₃H₂₈N₄O₇S
• 分子量: 624.674
• InChiKey: DNFCCJKRCJEIJX-BJVCMNDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  131.73
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine 在 间氯过氧苯甲酸 、 碳酸氢钠 作用下， 以 水 、 乙腈 、 氯仿 为溶剂， 反应 1.0h， 以95%的产率得到
  参考文献：
  名称：

  [EN] NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  [FR] DERIVES NUCLEOSIDIQUES DESTINES AU TRAITEMENT DE L'INFECTION PAR LE VIRUS DE L'HEPATITE C

  摘要：

  公开号：

  WO2003093290A3
• 作为产物：
  描述：

  ALPHA-D-赤式戊呋喃糖-2-酮 1,3,5-三苯甲酸酯 在 4-二甲氨基吡啶 、 cerium(III) chloride 、 三氟甲磺酸三甲基硅酯 、 牛血清白蛋白 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine
  参考文献：
  名称：

  2′-C-Alkylribonucleosides: Design, Synthesis, and Conformation

  摘要：

  Certain 2'-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed.

  DOI：

  10.1080/07328319708006205

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.