2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-1-phenylthio-β-D-4-thioribofuranose | 1132807-45-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-1-phenylthio-β-D-4-thioribofuranose
• 英文别名: [(4aR,6S,7R,7aS)-2,2-ditert-butyl-6-phenylsulfanyl-4a,6,7,7a-tetrahydro-4H-thieno[3,2-d][1,3,2]dioxasilin-7-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1132807-45-4
• 化学式: C₂₅H₄₄O₃S₂Si₂
• 分子量: 512.926
• InChiKey: ACQHRMKJGFOVCX-GXRSIYKFSA-N

物化性质

• 熔点：
  72-74 °C
• 沸点：
  517.2±50.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以232.9 mg的产率得到2-O-(t-butyldimethylsilyl)-3,5-O-(di-t-butylsilylene)-1-phenylthio-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

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.