methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside | 1467030-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside
• CAS: 1467030-45-0
• 化学式: C₅₁H₈₃NO₁₂Si₃
• 分子量: 986.476
• InChiKey: VOKXCNZPWCSMLP-FWNZECGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.51
• 重原子数：
  67.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  140.68
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 17.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-glucopyranosyl-(1→4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside
  参考文献：
  名称：

  Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor

  摘要：

  An assessment of the relative O-3/O-4 reactivities of both alpha- and beta-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a D-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.002
• 作为产物：
  描述：

  methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside 、 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 以43%的产率得到methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→3)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside
  参考文献：
  名称：

  Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor

  摘要：

  An assessment of the relative O-3/O-4 reactivities of both alpha- and beta-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a D-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.002