1-O-acetyl-2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose | 1132807-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 1-O-acetyl-2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose
• 英文别名: [(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] acetate
• CAS: 1132807-46-5
• 化学式: C₂₁H₄₂O₅SSi₂
• 分子量: 462.798
• InChiKey: ZRDRJDKJQMHMSD-BRSBDYLESA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  448.1±45.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 [(4aR,6S,7R,7aS)-6-bromo-2,2-ditert-butyl-4a,6,7,7a-tetrahydro-4H-thieno[3,2-d][1,3,2]dioxasilin-7-yl]oxy-tert-butyl-dimethylsilane
  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：

  2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-1-phenylthio-β-D-4-thioribofuranose 、 mercury(II) diacetate 在 溶剂黄146 作用下， 反应 14.0h， 以96%的产率得到1-O-acetyl-2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose
  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