1,4-anhydro-2-deoxy-3,5-O-(di-t-butylsilylene)-4-thio-D-erythro-pento-1-enitol 1-oxide | 1132807-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 1,4-anhydro-2-deoxy-3,5-O-(di-t-butylsilylene)-4-thio-D-erythro-pento-1-enitol 1-oxide
• CAS: 1132807-34-1
• 化学式: C₁₃H₂₄O₃SSi
• 分子量: 288.483
• InChiKey: KNZXEHNFVVKHER-WVQJBOLRSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  385.2±42.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-3,5-O-(di-t-butylsilylene)-4-thio-D-erythro-pento-1-enitol 1-oxide 、 乙酸酐 在 三甲基硅乙酸酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 1,2-di-O-acetyl-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose 、 1,2-di-O-acetyl-3,5-O-(di-t-butylsilylene)-α-D-4-thioribofuranose 、 、 [(2R,3S,4R,5R)-4,5-diacetyloxy-2-[[ditert-butyl(fluoro)silyl]oxymethyl]thiolan-3-yl] acetate 、 、 [(2R,3S,4R,5R)-4,5-diacetyloxy-2-[[acetyloxy(ditert-butyl)silyl]oxymethyl]thiolan-3-yl] acetate
  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：

  1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-4-thio-D-erythro-pento-1-enitol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,4-anhydro-2-deoxy-3,5-O-(di-t-butylsilylene)-4-thio-D-erythro-pento-1-enitol 1-oxide 、 1,4-anhydro-2-deoxy-3,5-O-(di-t-butylsilylene)-4-thio-D-erythro-pento-1-enitol 1-oxide
  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