(E)-S-phenyl 3-((2R,3S,4R,5R)-3,4-bis(tert-butyldimethylsilyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate | 911826-87-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (E)-S-phenyl 3-((2R,3S,4R,5R)-3,4-bis(tert-butyldimethylsilyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate
• 英文别名: S-phenyl (E)-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]prop-2-enethioate
• CAS: 911826-87-4
• 化学式: C₂₉H₄₄N₂O₆SSi₂
• 分子量: 604.915
• InChiKey: WIFMMARWWLDBRY-YDTGGBKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-S-phenyl 3-((2R,3S,4R,5R)-3,4-bis(tert-butyldimethylsilyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate 在 硫化氢 、 二甲基二环氧乙烷 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 1-((2R,3R,4R,5S)-3,4-bis(tert-butyldimethylsilyloxy)-5-((S)-[5-(2,5-dioxo-1,2-dithiolan-3-yl)]-tetrahydrofuran-2-yl)pyrimidine)-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues

  摘要：

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.

  DOI：

  10.1021/jm060471h
• 作为产物：
  描述：

  2',3'-bis-O-(tert-butyldimethylsilyl)uridine 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 49.25h， 生成 (E)-S-phenyl 3-((2R,3S,4R,5R)-3,4-bis(tert-butyldimethylsilyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues

  摘要：

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.

  DOI：

  10.1021/jm060471h

文献信息

• Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues
  作者：Ákos Szilágyi、Ferenc Fenyvesi、Orsolya Majercsik、István F. Pelyvás、Ildikó Bácskay、Pálma Fehér、Judit Váradi、Miklós Vecsernyés、Pál Herczegh

  DOI：10.1021/jm060471h

  日期：2006.9.1

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.