p-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1 -> 3)-4,6-di-tert-butylsilanediyl-β-D-mannopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 309929-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1 -> 3)-4,6-di-tert-butylsilanediyl-β-D-mannopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1-> 3)-4,6-di-tert-butylsilanediyl-β-D-mannopyranosyl-(1-> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 309929-69-9
• 化学式: C₇₈H₈₉NO₁₉Si
• 分子量: 1372.65
• InChiKey: SPORUWMTLDBLRY-SMOBXBHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.62
• 重原子数：
  99.0
• 可旋转键数：
  26.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  213.13
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸三甲基硅酯 、 p-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1 -> 3)-4,6-di-tert-butylsilanediyl-β-D-mannopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of a novel asparagine-linked heptasaccharide structure via p-methoxybenzyl-assisted β-mannosylation

  摘要：

  Synthesis of a core heptasaccharide asparagine N-4-(alpha-D-mannopyranosyl-(1 --> 6)-[(alpha-D-mannopyranosyl)-(1 --> 3)]-[(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 2)]-(beta-D-mannopyranosyl)-(1 --> 4)-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 4)-[(alpha-L-fucopyranosyl)-(1 --> 6)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine (1a) found from CHO glycosylation mutant cell LEC 1 4 is described. The structure of la is highly novel in terms of the presence of an extra GlcNAc residue linked to the 2 position of beta-linked mannose. The synthesis was performed using p-methoxybenzyl-assisted intramolecular aglycon delivery as the key transformation. 4,6-O-TIDPS-protected thiomannoside methyl 2-O-p-methoxybenzyl-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-3-O-trimethylsilyl-1-thio-alpha-D-mannopyranoside was adopted for this particular purpose, in which afforded beta-mannoside p-methoxyphenyl 2,3-O-(p-methoxybenzylidene)-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-beta-D-mannopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside stereoselectively in 75% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00123-3
• 作为产物：
  描述：

  p-methoxyphenyl O-[2,3-O-(p-methoxybenzylidene)-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-β-D-mannopyranosyl]-(1-> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.75h， 生成 p-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1 -> 3)-4,6-di-tert-butylsilanediyl-β-D-mannopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a novel asparagine-linked heptasaccharide structure via p-methoxybenzyl-assisted β-mannosylation

  摘要：

  Synthesis of a core heptasaccharide asparagine N-4-(alpha-D-mannopyranosyl-(1 --> 6)-[(alpha-D-mannopyranosyl)-(1 --> 3)]-[(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 2)]-(beta-D-mannopyranosyl)-(1 --> 4)-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 4)-[(alpha-L-fucopyranosyl)-(1 --> 6)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine (1a) found from CHO glycosylation mutant cell LEC 1 4 is described. The structure of la is highly novel in terms of the presence of an extra GlcNAc residue linked to the 2 position of beta-linked mannose. The synthesis was performed using p-methoxybenzyl-assisted intramolecular aglycon delivery as the key transformation. 4,6-O-TIDPS-protected thiomannoside methyl 2-O-p-methoxybenzyl-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-3-O-trimethylsilyl-1-thio-alpha-D-mannopyranoside was adopted for this particular purpose, in which afforded beta-mannoside p-methoxyphenyl 2,3-O-(p-methoxybenzylidene)-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-beta-D-mannopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside stereoselectively in 75% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00123-3