1-[5-tert-butyldiphenylsilyl-2,3-dideoxy-3-thio-3-S-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]-thymine | 926656-50-0

• 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-tert-butyldiphenylsilyl-2,3-dideoxy-3-thio-3-S-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]-thymine
• CAS: 926656-50-0
• 化学式: C₅₂H₅₂N₂O₁₁SSi
• 分子量: 941.143
• InChiKey: MEBJQCPHVNDVQC-IOVBOKGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 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：
  161.45
• 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-tert-butyldiphenylsilyl-2,3-dideoxy-3-thio-3-S-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]-thymine 在 四丁基氟化铵 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 125.0h， 生成 1-(3-S-β-D-ribofuranosyl-2,3-dideoxy-3-thio-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：

  5'-O-tert-butyldiphenylsilylthymidine 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 四氯化锡 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-[5-tert-butyldiphenylsilyl-2,3-dideoxy-3-thio-3-S-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-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