Acetic acid (2R,3S,5R)-5-[5-(3-tert-butyldisulfanyl-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2-hydroxymethyl-tetrahydro-furan-3-yl ester | 647852-38-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Acetic acid (2R,3S,5R)-5-[5-(3-tert-butyldisulfanyl-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2-hydroxymethyl-tetrahydro-furan-3-yl ester
• 英文别名: 3'-O-Acetyl-5-[3-(tert-butyldisulfanyl)prop-1-yn-1-yl]-2'-deoxyuridine；[(2R,3S,5R)-5-[5-[3-(tert-butyldisulfanyl)prop-1-ynyl]-2,4-dioxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 647852-38-8
• 化学式: C₁₈H₂₄N₂O₆S₂
• 分子量: 428.53
• InChiKey: SZVWSNZJZQYYQF-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5R)-5-[5-(3-tert-butyldisulfanyl-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2-hydroxymethyl-tetrahydro-furan-3-yl ester 在 ammonium hydroxide 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 水 为溶剂， 反应 1.59h， 生成
  参考文献：
  名称：

  C-5 Modified Nucleosides: Direct Insertion of Alkynyl-Thio Functionality in Pyrimidines

  摘要：

  A route is presented to append, in a single step, alkynyl thioesters to the 5-position of a pyrimidine ring of a nucleoside that is unprotected. These products should be useful to support in vitro selection experiments with functionalized DNA.

  DOI：

  10.1081/ncn-120022030
• 作为产物：
  描述：

  5-(3-acetylthio-1-propynyl)-2'-deoxyuridine 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 Acetic acid (2R,3S,5R)-5-[5-(3-tert-butyldisulfanyl-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2-hydroxymethyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  C-5 Modified Nucleosides: Direct Insertion of Alkynyl-Thio Functionality in Pyrimidines

  摘要：

  A route is presented to append, in a single step, alkynyl thioesters to the 5-position of a pyrimidine ring of a nucleoside that is unprotected. These products should be useful to support in vitro selection experiments with functionalized DNA.

  DOI：

  10.1081/ncn-120022030

文献信息

• C-5 Modified Nucleosides: Direct Insertion of Alkynyl-Thio Functionality in Pyrimidines
  作者：Heike A. Held、Abhijit Roychowdhury、Steven A. Benner

  DOI：10.1081/ncn-120022030

  日期：2003.7.1

  A route is presented to append, in a single step, alkynyl thioesters to the 5-position of a pyrimidine ring of a nucleoside that is unprotected. These products should be useful to support in vitro selection experiments with functionalized DNA.