methyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside | 1381857-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-4)[Bz(-2)][Bz(-3)][Bz(-6)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1381857-80-2
• 化学式: C₅₅H₅₄O₁₃
• 分子量: 923.026
• InChiKey: MHTDTRHCXYQWSY-GIQRWTIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  68
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 、 p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 在 1-(p-tolylthio)azepan-2-one 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以92%的产率得到methyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf

  摘要：

  N-(p-Methylphenylthio)-epsilon-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.024

文献信息

• Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf
  作者：Sajal Kumar Maity、Nabamita Basu、Rina Ghosh

  DOI：10.1016/j.carres.2012.03.024

  日期：2012.6

  N-(p-Methylphenylthio)-epsilon-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy. (C) 2012 Elsevier Ltd. All rights reserved.