2-[2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranosyl]thiazole-4-carboxamide | 1132807-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranosyl]thiazole-4-carboxamide
• 英文别名: 2-[(4aR,6R,7R,7aS)-2,2-ditert-butyl-7-[tert-butyl(dimethyl)silyl]oxy-4a,6,7,7a-tetrahydro-4H-thieno[3,2-d][1,3,2]dioxasilin-6-yl]-1,3-thiazole-4-carboxamide
• CAS: 1132807-49-8
• 化学式: C₂₃H₄₂N₂O₄S₂Si₂
• 分子量: 530.9
• InChiKey: PTXRJLVNMYCIQY-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranosyl]thiazole-4-carboxamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以94%的产率得到4'-thiotiazofurin
  参考文献：
  名称：

  Additive Pummerer Reaction of 3,5-O-(Di-tert-butyl)silylene-4-thiofuranoid Glycal: A High-Yield and β-Selective Entry to 4′-Thioribonucleosides

  摘要：

  Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac2O/TMSOAc/BF3 center dot OEt2 in CH2Cl2, the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7. Compound 7 serves as a highly beta-selective glycosyl donor in the Vorbruggen condensation carried out in the presence of TMSOTf. Thus, the 4-thio-beta-D-ribofuranosyl derivatives of uracil, thymine, N-4-acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized. The use of 7 can be extended to the beta-selective synthesis of 4'-thio-C-ribonucleosides.

  DOI：

  10.1021/jo802615h
• 作为产物：
  描述：

  ethyl 2-[2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranosyl]thiazole-4-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以99%的产率得到2-[2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranosyl]thiazole-4-carboxamide
  参考文献：
  名称：

  Additive Pummerer Reaction of 3,5-O-(Di-tert-butyl)silylene-4-thiofuranoid Glycal: A High-Yield and β-Selective Entry to 4′-Thioribonucleosides

  摘要：

  Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac2O/TMSOAc/BF3 center dot OEt2 in CH2Cl2, the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7. Compound 7 serves as a highly beta-selective glycosyl donor in the Vorbruggen condensation carried out in the presence of TMSOTf. Thus, the 4-thio-beta-D-ribofuranosyl derivatives of uracil, thymine, N-4-acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized. The use of 7 can be extended to the beta-selective synthesis of 4'-thio-C-ribonucleosides.

  DOI：

  10.1021/jo802615h

文献信息

• Additive Pummerer Reaction of 3,5-<i>O</i>-(Di-<i>tert</i>-butyl)silylene-4-thiofuranoid Glycal: A High-Yield and β-Selective Entry to 4′-Thioribonucleosides
  作者：Kazuhiro Haraguchi、Hiromitsu Matsui、Shin Takami、Hiromichi Tanaka

  DOI：10.1021/jo802615h

  日期：2009.3.20

  Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac2O/TMSOAc/BF3 center dot OEt2 in CH2Cl2, the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7. Compound 7 serves as a highly beta-selective glycosyl donor in the Vorbruggen condensation carried out in the presence of TMSOTf. Thus, the 4-thio-beta-D-ribofuranosyl derivatives of uracil, thymine, N-4-acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized. The use of 7 can be extended to the beta-selective synthesis of 4'-thio-C-ribonucleosides.