O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide | 218961-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS: 218961-16-1
• 化学式: C₄₈H₄₈N₄O₁₀
• 分子量: 840.93
• InChiKey: VZKVEYMNCXGWJC-VMZXAGSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  62.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  170.98
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 、 O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-O-<(2-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)>-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl) trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-O-<(2-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)>-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)>-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)>-3,6-di...
  参考文献：
  名称：

  p-Methoxybenzylidene-tetheredβ-Mannosylation for Stereoselective Synthesis of Asparagine-Linked Glycan Chains

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u
• 作为产物：
  描述：

  4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 在 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 四丁基溴化铵 、 sodium hydride 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
  参考文献：
  名称：

  p-Methoxybenzylidene-tetheredβ-Mannosylation for Stereoselective Synthesis of Asparagine-Linked Glycan Chains

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u

文献信息

• Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation
  作者：Chen Zeng、Bin Sun、Xuefeng Cao、Hailiang Zhu、Olawale Micheal Oluwadahunsi、Ding Liu、He Zhu、Jiabin Zhang、Qing Zhang、Gaolan Zhang、Christopher Andrew Gibbons、Yunpeng Liu、Jun Zhou、Peng George Wang

  DOI：10.1021/acs.orglett.0c02971

  日期：2020.11.6

  We report herein an efficient chemical synthesis of homogeneous human E-cadherin N-linked glycopeptides consisting of a heptapeptide sequence adjacent to the Asn-633 N-glycosylation site with representative N-glycan structures, including a conserved trisaccharide, a core-fucosylated tetrasaccharide, and a complex-type biantennary octasaccharide. The key steps are a chemoselective on-resin aspartylation

  我们在此报告了均质人 E-钙粘蛋白 N-连接糖肽的有效化学合成，该糖肽由与具有代表性 N-聚糖结构的 Asn-633 N-糖基化位点相邻的七肽序列组成，包括保守的三糖、核心岩藻糖基化四糖、和复合型双触角八糖。关键步骤是使用含假脯氨酸的肽进行化学选择性树脂上天冬氨酸化和使用糖基氟作为供体的立体选择性糖基化。这种合成策略证明了在获取广泛的同质 N 连接糖肽以检查其生物学功能方面的潜在效用。
• Synthesis of a novel asparagine-linked heptasaccharide structure via p-methoxybenzyl-assisted β-mannosylation
  作者：Yuki Ohnishi、Hiromune Ando、Tsubasa Kawai、Yoshiaki Nakahara、Yukishige Ito

  DOI：10.1016/s0008-6215(00)00123-3

  日期：2000.9

  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.