1,2-di-O-acetyl-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose | 1132807-36-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-di-O-acetyl-3,5-O-(di-t-butylsilylene)-β-D-4-thioribofuranose
• 英文别名: [(4aR,6R,7R,7aS)-6-acetyloxy-2,2-ditert-butyl-4a,6,7,7a-tetrahydro-4H-thieno[3,2-d][1,3,2]dioxasilin-7-yl] acetate
• CAS: 1132807-36-3
• 化学式: C₁₇H₃₀O₆SSi
• 分子量: 390.573
• InChiKey: DXNOBUNHHWTQCZ-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 1,4-anhydro-2-deoxy-3,5-O-(di-t-butylsilylene)-4-thio-D-erythro-pento-1-enitol 1-oxide 、 乙酸酐 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 、 1-O-acetyl-3,5-O-(di-t-butylsilylene)-2-O-(trifluoromethanesulfonyl)-β-D-4-thioribofuranose 、 1-O-acetyl-3,5-O-(di-t-butylsilylene)-2-O-(trifluoromethanesulfonyl)-α-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