1-<3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl>thymine | 181423-17-6

• 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-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl>thymine
• 英文别名: 1-[3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyoxolan-2-yl]methyl benzoate
• CAS: 181423-17-6
• 化学式: C₃₆H₃₄N₂O₁₂
• 分子量: 686.672
• InChiKey: YASAOYGSDVYLMT-TVNPJZNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  181.68
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-<3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl>thymine 在 氨 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以99%的产率得到O-β-D-ribofuranosyl-(1''-3')-thymidine
  参考文献：
  名称：

  Ribosylation of Pyrimidine 2′-Deoxynucleosides

  摘要：

  The previously developed method for the preparation of 2'-O-D-ribofuranosyl-nucleosides is extended to ribosylation of 2'-deoxynucleosides. The scope and limitations of this reaction are discussed.

  DOI：

  10.1080/07328319608002433
• 作为产物：
  描述：

  5'-O-tert-butyldiphenylsilylthymidine 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-<3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl>thymine
  参考文献：
  名称：

  Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars

  摘要：

  A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thymine, has been prepared through condensation of a suitably protected derivative of 3'-thiothymidine with an activated ribose sugar. NMR has been used to study the conformation of the S-disaccharide and the unmodified O-disaccharide. A full pseudorotational analysis showed that for the S-disaccharide, the ribose and deoxy ribose sugars have a preference for the south and north pucker, respectively; which is the reverse of what is seen for the O-disaccharide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.007

文献信息

• Rodionov; Efimtseva; Fomicheva, Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 3, p. 179 - 185
  作者：Rodionov、Efimtseva、Fomicheva、Padyukova、Mikhailov

  DOI：——

  日期：——
• Synthesis and Properties of Phosphorylated 3′-<i>O</i>-<font>β</font>-<scp>D</scp>-Ribofuranosyl-2′-deoxythymidine
  作者：Ekaterina V. Efimtseva、Alexandra A. Shelkunova、Sergey N. Mikhailov、Koen Nauwelaerts、Jef Rozenski、Eveline Lescrinier、Piet Herdewijn

  DOI：10.1081/ncn-120022028

  日期：2003.7.1

  A strategy was developed for the synthesis of 3'-O-beta-D-ribofuranosyl 2'-deoxythymidine derivatives using three different protecting groups, which allows the synthesis of a phosphoramidite building block for oligonucleotide synthesis. Likewise the 5'-O- and 5"-O-phosphorylated analogues were synthesized and their conformation was determined using NMR spectroscopy.