phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside | 1621691-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside
• CAS: 1621691-61-9
• 化学式: C₂₉H₃₇F₃O₆SSi
• 分子量: 598.756
• InChiKey: NFAXTVWHTRMPCH-HIQYAUPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside 、 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以9.091%的产率得到
  参考文献：
  名称：

  The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation

  摘要：

  The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The 'matching' in the donor-acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon-convenient building blocks for the preparation of neoglycoconjugates.

  DOI：

  10.1016/j.carres.2014.05.017
• 作为产物：
  描述：

  phenyl 3,5-di-O-benzoyl-1-thio-α-D-arabinofuranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 sodium methylate 、 sodium 2,2,2-trifluoroacetate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation

  摘要：

  The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The 'matching' in the donor-acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon-convenient building blocks for the preparation of neoglycoconjugates.

  DOI：

  10.1016/j.carres.2014.05.017