phenyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-mannopyranoside | 1555483-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-mannopyranoside
• CAS: 1555483-70-9
• 化学式: C₂₀H₃₂O₅SSi
• 分子量: 412.623
• InChiKey: GAZYYYRRWLYLOG-SFFUCWETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-mannopyranoside 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以50%的产率得到phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  β-Selective Mannosylation with a 4,6-Silylene-Tethered Thiomannosyl Donor

  摘要：

  Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-alpha-D-mannopyranoside (6) have been found to be beta-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the beta-mannoside is formed from beta-selective glycosylation of the oxocarbenium ion 25 in a B-2,B-5 conformation.

  DOI：

  10.1021/ol403722f
• 作为产物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 、 phenyl 1-thio-β-D-mannopyranoside 在 吡啶 作用下， 反应 1.0h， 以74%的产率得到phenyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  β-Selective Mannosylation with a 4,6-Silylene-Tethered Thiomannosyl Donor

  摘要：

  Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-alpha-D-mannopyranoside (6) have been found to be beta-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the beta-mannoside is formed from beta-selective glycosylation of the oxocarbenium ion 25 in a B-2,B-5 conformation.

  DOI：

  10.1021/ol403722f