(desoxy-3-methylidene-3'-β-D-erythro-pentofurannosyl)-9-adenine | 78151-96-9

• 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: (desoxy-3-methylidene-3'-β-D-erythro-pentofurannosyl)-9-adenine
• 英文别名: 3'-deoxy-3'-methyleneadenosine；(2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-4-methylideneoxolan-3-ol
• CAS: 78151-96-9
• 化学式: C₁₁H₁₃N₅O₃
• 分子量: 263.256
• InChiKey: SDGYZEXDBFSBRI-AZTOOPQRSA-N

物化性质

• 沸点：
  635.5±65.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (desoxy-3-methylidene-3'-β-D-erythro-pentofurannosyl)-9-adenine 在 吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  3'-脱氧腺苷-3'-螺环丙烷，3'-脱氧尿苷-3'-螺环丙烷和5'-脱氧-4'，5'-甲基腺苷的合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)73206-0
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 四丁基氟化铵 、 sodium tert-pentoxide 作用下， 以 四氢呋喃 为溶剂， 反应 54.0h， 生成 (desoxy-3-methylidene-3'-β-D-erythro-pentofurannosyl)-9-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

• Nucleic acid related compounds. 77. 2′,3′-Didehydro-2′,3′-dideoxy-2′(and 3′)-methylnucleosides via [3,3]-sigmatropic rearrangements of 2′(and 3′)-methylene-3′(and 2′)-<i>O</i>-thiocarbonyl derivatives and radical reduction of a 2′-chloro-3′-methylene analogue
  作者：Vincente Samano、Morris J. Robins

  DOI：10.1139/v93-027

  日期：1993.2.1

  Treatment of 5′-O-(tert-butyldiphenylsilyl)-2′(and 3′)-deoxy-2′(and 3′)-methyleneuridine (and adenosine) derivatives with phenyl chlorothionocarbonate gave the 3′(and 2′)-O-phenoxythiocarbonyl intermediates, which underwent spontaneous [3,3]-sigmatropic rearrangement to give the 2′,3′-didehydro-2′,3′-dideoxy-2′(and 3′)-(phenoxycarbonylthio)methyl analogues. These allylic thioesters were subjected to tributylstannane-mediated hydrodesulfurization and deprotection to give 2′,3′-didehydro-2′,3′-dideoxy-2′(and 3′)-methyluridine (and adenosine). Tributylstannane-mediated hydrodehalogenation of a 2′-chloro-2′,3′-dideoxy-3′-methyleneuridine derivative afforded the 2′,3′-didehydro-2′,3′-dideoxy-3′-methyl product of allylic transposition exclusively.

  对5'-O-(叔丁基二苯基硅基)-2'（和3'）-去氧-2'（和3'）-亚甲基尿苷（和腺苷）衍生物进行苯基氯硫代碳酸酯处理，得到3'（和2'）-O-苯氧硫酰中间体，这些中间体经历自发的[3,3]-sigmatropic重排反应，产生2'，3'-二去氢-2'，3'-二去氧-2'（和3'）-（苯氧羰基硫）甲基类似物。这些烯丙基硫酯经过三丁基锡介导的脱硫化和去保护作用，得到2'，3'-二去氢-2'，3'-二去氧-2'（和3'）-甲基尿苷（和腺苷）。对2'-氯-2'，3'-二去氧-3'-亚甲基尿苷衍生物进行三丁基锡介导的脱卤化反应，仅得到烯丙基转位的2'，3'-二去氢-2'，3'-二去氧-3'-甲基产物。
• Method for the treatment or prevention of flavivirus infections using nucleoside analogues
  申请人：——

  公开号：US20020019363A1

  公开（公告）日：2002-02-14

  The present invention relates to a method for the treatment or prevention of Flavivirus infections using nucleoside analogues in a host comprising administering a therapeutically effective amount of a compound having the formula I or a pharmaceutically acceptable salt thereof.

  本发明涉及一种使用核苷类似物在宿主体内治疗或预防黄病毒感染的方法，包括给予具有公式I或其药学上可接受的盐的治疗有效量的化合物。
• Un nouvel exemple de nucl�oside � sucre ramifi� insatur�: la d�soxy-3?-m�thylid�ne-3?-ad�nosine
  作者：Jean M. J. Tronchet、Jeannine F. Tronchet

  DOI：10.1002/hlca.19810640207

  日期：1981.3.18

  A Novel Example of Unsaturated Branched-chain Sugar Nucleoside: 3′-Deoxy-3′-methylidene-adenosine

  不饱和支链糖核苷的新例子：3'-脱氧-3'-亚甲基-腺苷
• Method for the treatment or prevention of Flavivirus infections using nucleoside analogues
  申请人：——

  公开号：US20040248844A1

  公开（公告）日：2004-12-09

  The present invention relates to a method for the treatment or prevention of Flavivirus infections using nucleoside analogues in a host comprising administering a therapeutically effective amount of a compound having the formula I or a pharmaceutically acceptable salt thereof.
• US6784161B2
  申请人：——

  公开号：US6784161B2

  公开（公告）日：2004-08-31