6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine | 137091-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine
• 英文别名: 6-N,N-dibenzoyl-9-[3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl]adenine；[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[6-(dibenzoylamino)purin-9-yl]-4-methylideneoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 137091-53-3
• 化学式: C₃₈H₄₁N₅O₇SSi
• 分子量: 739.924
• InChiKey: VRIRKHOYEVGSNF-BZLMBYDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  52.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  142.81
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以54%的产率得到6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-iodo-2-methylene-β-D-erythro-pentofuranosyl)adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 70. Synthesis of 2'(and 3')-deoxy-2'(and 3')-methyleneadenosines and bis(methylene)furan 4',5'-didehydro-5'-deoxy-2'(and 3')-methyleneadenosines. Inhibitors of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase

  摘要：

  Wittig treatment of 3',5'(or 2',5')-bis-O-silyl-2'(or 3')-ketoadenosine derivatives with methylenetriphenylphosphorane and deprotection gave the 2'(or 3')-deoxy-2'(or 3')-methyleneadenosines, respectively. Enzymatic deamination afforded the 2'(or 3')-deoxy-2'(or 3')-methyleneinosines. Treatment of 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methylene-5'-O-tosyladenosine (14) with sodium 2-methyl-2-butoxide and deprotection gave 9-(3,5-dideoxy-3-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (20). Analogous treatment of a protected 2',5'-dideoxy-5'-iodo-2'-methyleneadenosine derivative gave 9-(2,5-dideoxy-2-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (22). Biochemical aspects of the putative mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase by these compounds are discussed.

  DOI：

  10.1021/jo00025a029
• 作为产物：
  描述：

  (2R,3S,5R)-5-(6-氨基嘌呤-9-基)-2-(羟基甲基)-4-亚甲基四氢呋喃-3-醇 在 吡啶 、 咪唑 作用下， 反应 75.0h， 生成 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 70. Synthesis of 2'(and 3')-deoxy-2'(and 3')-methyleneadenosines and bis(methylene)furan 4',5'-didehydro-5'-deoxy-2'(and 3')-methyleneadenosines. Inhibitors of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase

  摘要：

  Wittig treatment of 3',5'(or 2',5')-bis-O-silyl-2'(or 3')-ketoadenosine derivatives with methylenetriphenylphosphorane and deprotection gave the 2'(or 3')-deoxy-2'(or 3')-methyleneadenosines, respectively. Enzymatic deamination afforded the 2'(or 3')-deoxy-2'(or 3')-methyleneinosines. Treatment of 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methylene-5'-O-tosyladenosine (14) with sodium 2-methyl-2-butoxide and deprotection gave 9-(3,5-dideoxy-3-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (20). Analogous treatment of a protected 2',5'-dideoxy-5'-iodo-2'-methyleneadenosine derivative gave 9-(2,5-dideoxy-2-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (22). Biochemical aspects of the putative mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase by these compounds are discussed.

  DOI：

  10.1021/jo00025a029