1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-thymine | 181423-05-2

• 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-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-thymine
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyoxolan-2-yl]methyl benzoate
• CAS: 181423-05-2
• 化学式: C₅₂H₅₂N₂O₁₂Si
• 分子量: 925.077
• InChiKey: BFSVTOYIFIURHN-AZNCQTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  67.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  170.68
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-thymine 在 四丁基氟化铵 作用下， 以 四氢呋喃 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
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 四氯化锡 作用下， 以 吡啶 、 1,2-二氯乙烷 为溶剂， 反应 5.67h， 生成 1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-thymine
  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

文献信息

• Effective Anomerisation of 2′‐Deoxyadenosine Derivatives During Disaccharide Nucleoside Synthesis
  作者：Irina V. Gulyaeva、Kari Neuvonen、Harri Lönnberg、Andrei A. Rodionov、Elena V. Shcheveleva、Georgii V. Bobkov、Ekaterina V. Efimtseva、Sergey N. Mikhailov

  DOI：10.1081/ncn-200040627

  日期：2004.1.12

  The formation of a disaccharide nucleoside (11) by O3'-glycosylation of 5'-O-protected 2'-deoxyadenosine or its N-6-benzoylated derivative has been observed to be accompanied by anomerisation to the corresponding alpha-anomeric product (12). The latter reaction can be explained by instability of the N-glycosidic bond of purine 2'-deoxynucleosides in the presence of Lewis acids. An independent study on the anomerisation of partly blocked 2'-deoxyadenosine has been carried out. Additionally, transglycosylation has been utilized in the synthesis of 3'-O-beta-D-ribofuranosyl-2'deoxyadenosines and its alpha-anomer.