3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate | 1258410-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate
• CAS: 1258410-90-0
• 化学式: C₃₅H₂₉NO₈S
• 分子量: 623.683
• InChiKey: XHTPHGNJNKGPHL-XVZOBNEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  121.15
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 methyl 2-O-benzyl-3, 4, 6-tri-O-benzoyl-D-glucopyranosyl-β-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 methyl 2-O-benzyl-3,4,6-tri-O-benzoyl-α-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl Alkoxythioimidates as Complementary Building Blocks for Chemical Glycosylation

  摘要：

  It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in

  DOI：

  10.1021/ol1023079
• 作为产物：
  描述：

  1,3,4,6-tetra-O-benzoyl-2-O-benzyl-D-glucopyranose 在 甲醇 、 18-冠醚-6 、 乙酰溴 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.5h， 生成 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate
  参考文献：
  名称：

  Glycosyl Alkoxythioimidates as Complementary Building Blocks for Chemical Glycosylation

  摘要：

  It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in

  DOI：

  10.1021/ol1023079