9-(2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine | 137058-76-5

• 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: 9-(2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine
• 英文别名: 2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methyleneadenosine；9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl]adenine
• CAS: 137058-76-5
• 化学式: C₂₃H₄₁N₅O₃Si₂
• 分子量: 491.781
• InChiKey: SZWZMQJCWXSRGS-HGHGUNKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  97.31
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  9-(2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine 在 水 、 三氟乙酸 作用下， 反应 0.5h， 以95%的产率得到9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-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：

  2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 在 吡啶 、 chromium(VI) oxide 、 乙酸酐 、 sodium tert-pentoxide 作用下， 以 二氯甲烷 为溶剂， 反应 52.5h， 生成 9-(2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-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

文献信息

• Synthesis of 3′-deoxyadenosine-3′-spirocyclopropane, 3′-deoxy-uridine-3′-spirocyclopropane, and 5′-deoxy-4′,5′-methanoadenosine
  作者：Vicente Samano、Morris J. Robins

  DOI：10.1016/s0040-4039(00)73206-0

  日期：1994.5

  Cycloaddition of diazomethane with 3′-deoxy-3′-methylene- and 4′,5′-didehydro-5′-deoxynucleoside derivatives followed by sensitized photochemical extrusion of nitrogen provided the previously unreported 3′- and 4′-spirocyclopropane nucleoside derivatives. Enhancement of the cycloaddition reactions by electron withdrawing benzoyl protecting groups was observed.

  将重氮甲烷与3'-脱氧-3'-亚甲基-和4'，5'-二氢-5'-脱氧核苷衍生物进行环加成反应，然后对氮进行敏化光化学挤出，可提供先前未报道的3'-和4'-螺环丙烷核苷衍生物。观察到通过吸电子苯甲酰基保护基团的环加成反应的增强。