2-azidoethyl (2,6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 316820-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl (2,6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 316820-49-2
• 化学式: C₅₂H₅₉N₃O₁₁
• 分子量: 902.054
• InChiKey: CHKXMLITJWDOMZ-JNUFLZOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.86
• 重原子数：
  66.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  150.29
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-azidoethyl (2,6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到2-azidoethyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  具有各种糖负载量的路易斯b六糖及其方酸-HSA共轭物的合成。

  摘要：

  Lewis b六糖，α-L-Fucp-（1-> 2）-β-D-Galp-（1-> 3）-[α-L-Fucp-（1-> 4）]-β -D-GlcpNAc-（1→3）-β-D-Galp-（1→4）-β-D-Glcp已经使用收敛合成法合成。从乙基4,6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚胺-1-硫代-β-D-吡喃葡萄糖苷开始，通过与糖基溴化物供体的两次正交糖基化，构建了硫代糖苷四糖供体嵌段。首先，使用三氟甲磺酸银作为促进剂引入半乳糖部分，然后在卤化物辅助条件下引入两个岩藻糖残基。最后，将该四糖以DMTST促进的偶联方式连接到带有间隔基的3I，4I-二醇乳糖受体上，以在脱保护后得到带有2-氨基乙基间隔基的衍生物Lewis b六糖。这与人类血清白蛋白（HSA）偶联，

  DOI：

  10.1016/s0008-6215(00)00189-0
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 氢溴酸 、 sodium methylate 、 氰化汞 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 mercury dibromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 122.0h， 生成 2-azidoethyl (2,6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  具有各种糖负载量的路易斯b六糖及其方酸-HSA共轭物的合成。

  摘要：

  Lewis b六糖，α-L-Fucp-（1-> 2）-β-D-Galp-（1-> 3）-[α-L-Fucp-（1-> 4）]-β -D-GlcpNAc-（1→3）-β-D-Galp-（1→4）-β-D-Glcp已经使用收敛合成法合成。从乙基4,6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚胺-1-硫代-β-D-吡喃葡萄糖苷开始，通过与糖基溴化物供体的两次正交糖基化，构建了硫代糖苷四糖供体嵌段。首先，使用三氟甲磺酸银作为促进剂引入半乳糖部分，然后在卤化物辅助条件下引入两个岩藻糖残基。最后，将该四糖以DMTST促进的偶联方式连接到带有间隔基的3I，4I-二醇乳糖受体上，以在脱保护后得到带有2-氨基乙基间隔基的衍生物Lewis b六糖。这与人类血清白蛋白（HSA）偶联，

  DOI：

  10.1016/s0008-6215(00)00189-0

文献信息

• Synthesis of Aminoethyl Glycosides of the Ganglioside GM₁and Asialo-GM₁Oligosaccharide Chains
  作者：P. E. Cheshev、E. A. Khatuntseva、Yu. E. Tsvetkov、A. S. Shashkov、N. E. Nifantiev

  DOI：10.1023/b:rubi.0000015775.24385.a0

  日期：2004.1

  4'-O-Glycosylation of 2-azidoethyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-6-O-benzoyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside with a disaccharide donor, 4-trichloroacetamidophenyl 4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1-thio-2-trichloroacetamido-beta-D-galactopyranoside, in dichloromethane in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid resulted in a tetrasaccharide, 2-azidoethyl (2,3,4,6-tetra-O-acetyl-beta-D-(galactopyranosyl)-(1 --> 3)-(4,6-di-O-acetyl-2-deoxy-2-trichloroacetamido-beta-D-galactopyranosyl)-(1 --> 4)-(2,3-di-O-benzyl-6-O-benzoyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside, in 69% yield. The complete removal of O-protecting groups in the tetrasaccharide, the replacement of N-trichloroacetyl by N-acetyl group, and the reduction of the aglycone azide group to amine led to the target aminoethyl glycoside of beta-D-Gal-(1 --> 3)-beta-D-Gal-NAc-(1 --> 4)-beta-D-Gal-(1 --> 4)-beta-D-Glc-OCH2CH2NH2 containing the oligosaccharide chain of asialo-GM(1) ganglioside in 72% overall yield. Selective 3'-O-glycosylation of 2-azidoethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside with thioglycoside methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha-D-galacto-2-nonulopyranosyl)oate in acetonitrile in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid afforded 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosyl)oate]-(2 --> 3)-2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside, the selectively protected derivative of the oligosaccharide chain of GM(3) ganglioside, in 79% yield. Its 4'-O-glycosylation with a disaccharide glycosyl donor, (4-trichloroacetophenyl-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) 1-thio-2-trichloroacetamido-beta-D-galactopyranoside in dichloromethane in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid gave 2-azidoethyl (2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 --> 3)-4,6-di-O-acetyl-2-deoxy-2-trichloroacetamido-beta-D-galactopyranosyl)-(1 --> 4)-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosyl)onate]-(2 --> 3)}-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside in 85% yield. The resulting pentasaccharide was O-deprotected, its N-trichloroacetyl group was replaced by N-acetyl group, and the aglycone azide group was reduced to afford in 85% overall yield aminoethyl glycoside of beta-D-Gal-(1 --> 3)-beta-D-GalNAc-(1 --> 4)-[alpha-D-Neu5Ac-(2 --> 3)]-beta-D-Gal-(1 --> 4)-beta-D-Glc-OCH2CH2NH2 containing the oligosaccharide chain of GM(1) ganglioside.