2-azidoethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside | 230286-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside
• 英文别名: 2-azidoethyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside；2-azidoethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 230286-12-1
• 化学式: C₁₇H₂₉N₃O₁₁
• 分子量: 451.431
• InChiKey: BRWHJBLIYDDMIT-WRMIZQQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.26
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  205.29
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-azidoethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 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 、 对甲苯磺酸 、 溶剂黄146 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 118.0h， 生成 2-azidoethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-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 oligosaccharide fragments of the Streptococcus pneumoniae type 14 capsular polysaccharide and their neoglycoconjugates with bovine serum albumin
  作者：E. V. Sukhova、D. V. Yashunsky、Yu. E. Tsvetkov、E. A. Kurbatova、N. E. Nifantiev

  DOI：10.1007/s11172-014-0462-5

  日期：2014.2

  2-Aminoethyl glycosides of tetra-, hexa- and octasaccharide fragments of the bacteria Streptococcus pneumoniae type 14 capsular polysaccharide were synthesized within a project directed to the development of pneumococcal conjugated vaccine based on synthetic carbohydrate ligands. Squarate method was used to obtain neoglycoconjugates of the synthesized oligosaccharides with bovine serum albumin.

  合成了肺炎链球菌14型荚膜多糖的四糖、六糖和八糖片段的2-氨乙基糖苷，这项工作是为了开发基于合成碳水化合物配体的肺炎球菌结合疫苗。采用方形酸法获得了合成的寡糖与牛血清白蛋白的新糖结合物。
• Synthesis of mono- and di-O-sulfates of spacer-armed lactose
  作者：M. A. Sablina、A. B. Tuzikov、T. V. Ovchinnikova、I. V. Mikhura、N. V. Bovin

  DOI：10.1007/s11172-015-0989-0

  日期：2015.5

  A series of spacer-armed lactose derivatives with one or two O-sulfo groups in various positions, namely, 6-O-Su-Lac, 3´,6-O-Su2-Lac, 6´-O-Su-Lac, 6,6´-O-Su2-Lac, and 3´-O-Su-Lac (Su = SO3H), was synthesized starting from the same precursor. All sulfated disaccharides were obtained in the form of 2-aminoethyl glycosides.

  从相同的前体开始，合成了一系列在不同位置带有一个或两个 O-硫基的间隔臂乳糖衍生物，即 6-O-Su-Lac、3´,6-O-Su2-Lac、6´-O-Su-Lac、6,6´-O-Su2-Lac 和 3´-O-Su-Lac （Su = SO3H）。所有硫酸化二糖都以 2-氨基乙基糖苷的形式获得。
• Synthesis of 2-aminoethyl 3′-(N-glycolylneuraminyl)-β-actoside and neoglycoconjugates based thereon — a prototype of a cancer vaccine and artificial antigens for the control of immune response
  作者：E. A. Khatuntseva、Yu. E. Tsvetkov、R. N. Stepanenko、R. Ya. Vlasenko、R. V. Petrov、N. E. Nifantiev

  DOI：10.1007/s11172-010-0032-4

  日期：2009.2

  The 2-aminoethyl β-glycoside of the trisaccharide 3′-(N-glycolylneuraminyl)lactose was synthesized in the framework of studies of approaches to the preparation of synthetic tumor vaccines based on carbohydrate chains of tumor-associated gangliosides and converted to the corresponding 2-4-maleimidobutanoylamino)ethyl glycoside. The reaction of the latter with thiolated hemocyanin from the keyhole limpet Megathura crenulata (KLH) gave a carbo-hydrate—protein conjugate, a tumor vaccine prototype containing about 250 trisaccharide ligands attached to a macromolecular KLH complex. A polyvalent conjugate with a polyacryl-amide support was synthesized to be used as a coating antigen in the control of specificity and efficiency of immune response by enzyme-linked immunosorbent assay (ELISA).

  在基于肿瘤相关神经节苷脂糖链的合成肿瘤疫苗制备方法研究的框架下，合成了三糖 3'-(N-甘氨酰神经氨酰基)乳糖的 2-氨基乙基 β-糖苷，并将其转化为相应的 2 -4-马来酰亚胺基丁酰氨基)乙基糖苷。后者与来自匙孔帽贝 Megathura crenulata (KLH) 的硫醇化血蓝蛋白反应产生碳水化合物-蛋白质缀合物，这是一种肿瘤疫苗原型，含有约 250 个连接到大分子 KLH 复合物的三糖配体。合成了具有聚丙烯酰胺支持物的多价缀合物，用作包被抗原，通过酶联免疫吸附测定（ELISA）控制免疫反应的特异性和效率。
• 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.