1-[3-deoxy-3-(hydroxymethyl)-β-L-ribofuranosyl]thymine

• 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: 1-[3-deoxy-3-(hydroxymethyl)-β-L-ribofuranosyl]thymine
• 英文别名: 1-[(2S,3S,4R,5R)-3-hydroxy-4,5-bis(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: SAQLIIXINWYWJX-GHCJXIJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[3-deoxy-3-(hydroxymethyl)-β-L-ribofuranosyl]thymine 在 重铬酸吡啶 作用下， 生成 1-[(2S,4S,5R)-4,5-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  SYNTHESIS OF NOVELD- ANDL-3′-DEOXY-3′-C-HYDROXYMETHYL NUCLEOSIDE WITH EXOCYCLIC METHYLENE AS POTENTIAL RIBONUCLEOTIDE REDUCTASE INHIBITOR

  摘要：

  D- and L-3'-Deoxy-3'-C-hydroxymethyl thymidine substituted with exocyclic methylene at 2'-position were synthesized, starting from D- and L-xylose as potential ribonucleotide reductase inhibitor, respectively, but they were found to be inactive against several tumor cell lines.

  DOI：

  10.1081/ncn-100002355
• 作为产物：
  描述：

  1-{3-deoxy-1,2,5-tri-O-acetyl-3-[(O-acetyl)-methyl]-β-L-ribofuranosyl}thymine 在 氨 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以53%的产率得到1-[3-deoxy-3-(hydroxymethyl)-β-L-ribofuranosyl]thymine
  参考文献：
  名称：

  L-3'-羟甲基核糖核苷的合成。

  摘要：

  通过关键的中间体碳水化合物8合成目标化合物，该化合物通过首先选择性地保护1'-和2'-羟基，然后选择性地甲苯磺酸化5'-羟基来合成化合物3。然后，制备甲苯磺酰基部分。将其用苄基取代以得到4。化合物4进行Dess-Martin氧化，得到酮5。将化合物5进行Wittig烯化反应，得到烯烃6，然后进行区域选择性氢硼化，得到7。化合物7用乙酸完全乙酰化。 ，乙酸酐和硫酸得到关键中间体8。

  DOI：

  10.1080/15257770008033005

文献信息

• SYNTHESIS OF NOVEL<scp>D</scp>- AND<scp>L</scp>-3′-DEOXY-3′-<i>C</i>-HYDROXYMETHYL NUCLEOSIDE WITH EXOCYCLIC METHYLENE AS POTENTIAL RIBONUCLEOTIDE REDUCTASE INHIBITOR
  作者：Moon Woo Chun、Myung Jung Kim、Un Hee Jo、Joong Hyup Kim、Hee-Doo Kim、Lak Shin Jeong

  DOI：10.1081/ncn-100002355

  日期：2001.3.31

  D- and L-3'-Deoxy-3'-C-hydroxymethyl thymidine substituted with exocyclic methylene at 2'-position were synthesized, starting from D- and L-xylose as potential ribonucleotide reductase inhibitor, respectively, but they were found to be inactive against several tumor cell lines.
• Synthesis of L-3′-Hydroxymethylribonucleosides
  作者：John S. Cooperwood、Vincent Boyd、Giuseppe Gumina、Chung K. Chu

  DOI：10.1080/15257770008033005

  日期：2000.1

  target compounds were synthesized via the key intermediate carbohydrate 8, which was synthesized by first selectively protecting the 1'- and 2'-hydroxyl groups followed by selective tosylation of the 5'-hydroxyl group to obtain compound 3. The tosyl moiety was then replaced by a benzyl either to obtain 4. Compound 4 underwent Dess-Martin oxidation to afford the ketone 5. Compound 5 was subjected to Wittig

  通过关键的中间体碳水化合物8合成目标化合物，该化合物通过首先选择性地保护1'-和2'-羟基，然后选择性地甲苯磺酸化5'-羟基来合成化合物3。然后，制备甲苯磺酰基部分。将其用苄基取代以得到4。化合物4进行Dess-Martin氧化，得到酮5。将化合物5进行Wittig烯化反应，得到烯烃6，然后进行区域选择性氢硼化，得到7。化合物7用乙酸完全乙酰化。 ，乙酸酐和硫酸得到关键中间体8。