[(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate | 193093-41-3

• 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: [(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate
• 英文别名: [(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-2-[(2-sulfanylidene-1,3,2λ5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate
• CAS: 193093-41-3
• 化学式: C₁₈H₂₄N₅O₇PS₂
• 分子量: 517.524
• InChiKey: YQCYJECQIWOABT-OAUZWUJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  200
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate 在 氨 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 dGTP(α-S)
  参考文献：
  名称：

  Synthesis of Nucleoside α-Thiotriphosphates via an Oxathiaphospholane Approach^†

  摘要：

  Nucleoside 5 '-O-(alpha-thiotriphosphates) were obtained in reactions of the appropriate nucleoside 5 '-O-(2-thio-1,3,2-oxathiaphospholanes) with pyrophosphate in the presence of DBU. The presented method allows also for preparation of alpha-seleno congeners and corresponding a-modified diphosphates.

  DOI：

  10.1021/ol050617r
• 作为产物：
  描述：

  2-氯-1,3,2-氧杂硫杂磷杂环戊烷 、 3'-O-acetyl-N2-isobutyryl-2'-deoxyguanosine 在 吡啶 、 sulfur 作用下， 反应 16.0h， 以81%的产率得到[(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate
  参考文献：
  名称：

  Synthesis of Nucleoside α-Thiotriphosphates via an Oxathiaphospholane Approach^†

  摘要：

  Nucleoside 5 '-O-(alpha-thiotriphosphates) were obtained in reactions of the appropriate nucleoside 5 '-O-(2-thio-1,3,2-oxathiaphospholanes) with pyrophosphate in the presence of DBU. The presented method allows also for preparation of alpha-seleno congeners and corresponding a-modified diphosphates.

  DOI：

  10.1021/ol050617r

文献信息

• Thiophosphorylation of Biologically Relevant Alcohols by the Oxathiaphospholane Approach
  作者：Magdalena Olesiak、Danuta Krajewska、Ewa Wasilewska、Dariusz Korczyński、Janina Baraniak、Andrzej Okruszek、Wojciech J. Stec

  DOI：10.1055/s-2002-31913

  日期：——

  2-Alkoxy-2-thiono-1,3,2-oxathiaphospholanes are readily transformed into phosphorothioate monoesters of the corresponding alcohols in a one-pot process, involving the reaction with 3-hydroxypropionitrile in the presence of DBU, followed by treatment with aqueous ammonia. In this way a series of nucleoside-3′-O- and 5′-O-phosphorothioates were prepared, as well as phosphorothioate derivatives of selected polyols.

  2-烷氧基-2-硫代-1,3,2-氧硫磷烷可以方便地通过一步法转化为相应醇的磷酸硫代单酯，该方法涉及在DBU存在下与3-羟基丙腈反应，随后用氨水处理。通过这种方法制备了一系列核苷-3′-O-和5′-O-磷酸硫代酯，以及选定多元醇的磷酸硫代衍生物。