3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 338744-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: 3-azidopropyl 4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-(3-azidopropoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 338744-49-3
• 化学式: C₅₀H₅₇N₃O₁₁
• 分子量: 876.016
• InChiKey: UZNMPZGJPZSJDN-IVZMCVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  64
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trichloroacetamido-D-glycero-D-galacto-2-nonulopyranosonate-2-(N-phenyl)-trifluoroacetimidate 、 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以33%的产率得到
  参考文献：
  名称：

  氨基丙基官能化神经节苷脂GM的全合成1个

  摘要：

  GM 1是存在于哺乳动物细胞表面的常见神经节苷脂五糖。已经表明它在细胞通讯和β-淀粉样蛋白聚集的起始中起重要作用。为了合成GM 1，通过[3 + 2]策略开发了有效的合成途径。使用传统的乙酰胺保护的唾液酸基硫糖基供体制备了在还原端带有叠氮丙基的GM 3三糖受体，该化合物的立体选择性比三氯乙酰胺或恶唑烷酮保护的唾液酸供体更好。GM 3轴向4-羟基的糖基化发现二糖供体的β-糖基化高度依赖于供体保护基。带有更刚性的亚苄基的供体给出低的糖基化产率。用乙酸酯取代亚苄基导致有效的偶联和完全保护的GM 1五糖的形成。通过氨基丙基侧链官能化的五糖产生的GM 1的脱保护，这将是生物学研究的宝贵探针。

  DOI：

  10.1007/s11426-011-4449-x
• 作为产物：
  描述：

  Lactose 在 甲醇 、 sodium azide 、 三氟化硼乙醚 、 sodium methylate 、 sodium acetate 、 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 3-azidopropyl (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：

  氨基丙基官能化神经节苷脂GM的全合成1个

  摘要：

  GM 1是存在于哺乳动物细胞表面的常见神经节苷脂五糖。已经表明它在细胞通讯和β-淀粉样蛋白聚集的起始中起重要作用。为了合成GM 1，通过[3 + 2]策略开发了有效的合成途径。使用传统的乙酰胺保护的唾液酸基硫糖基供体制备了在还原端带有叠氮丙基的GM 3三糖受体，该化合物的立体选择性比三氯乙酰胺或恶唑烷酮保护的唾液酸供体更好。GM 3轴向4-羟基的糖基化发现二糖供体的β-糖基化高度依赖于供体保护基。带有更刚性的亚苄基的供体给出低的糖基化产率。用乙酸酯取代亚苄基导致有效的偶联和完全保护的GM 1五糖的形成。通过氨基丙基侧链官能化的五糖产生的GM 1的脱保护，这将是生物学研究的宝贵探针。

  DOI：

  10.1007/s11426-011-4449-x

文献信息

• A Highly Convergent Synthesis of a Complex Oligosaccharide Derived from Group B Type III <i>Streptococcus</i>
  作者：Alexei V. Demchenko、Geert-Jan Boons

  DOI：10.1021/jo001477w

  日期：2001.4.1

  An efficient synthesis of a heptasaccharide derived from group B type III Streptococcus carrying an artificial spacer (1) is described. Rapid assembly of a protected heptasaccharide (16a) is accomplished from readily available building blocks 2-5 without a single protecting group manipulation between glycosylation steps. The synthetic strategy may be applied to the assembly of other branched complex

  描述了一种有效的合成带有人工间隔子（1）的B型III型链球菌衍生的七糖的方法。受保护的七糖（16a）的快速组装是从容易获得的结构单元2-5完成的，而无需在糖基化步骤之间进行单个保护基操作。合成策略可以应用于其他分支复杂寡糖的组装。将脱保护的七糖1与聚[N-（丙烯酰氧基）琥珀酰亚胺]偶联，所得物质将用于ELISA分析的开发，以检测针对孕妇的GBS III型抗体。
• Synthesis of 6-PEt<i>N</i>-α-D-Gal<i>p</i>NAc-(1–&gt;6)-β-D-Gal<i>p</i>-(1–&gt;4)-β-D-Glc<i>p</i>NAc-(1–&gt;3)-β-D-Gal<i>p</i>-(1–&gt;4)-β-D-Glc<i>p</i>, a <i>Haemophilus influenzae</i> lipopolysacharide structure, and biotin and protein conjugates thereof
  作者：Andreas Sundgren、Martina Lahmann、Stefan Oscarson

  DOI：10.3762/bjoc.6.80

  日期：——

  Background: In bacteria with truncated lipopolysaccharide structures, i.e., lacking the O-antigen polysaccharide part, core structures are exposed to the immune system upon infection and thus their use as carbohydrate surface antigens in glycoconjugate vaccines can be considered and investigated. One such suggested structure from Haemophilus influenzae LPS is the phosphorylated pentasaccharide 6-PEtN-α-D-GalpNAc-(1→6)-β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp.

  Results: Starting from a spacer-containing lactose derivative a suitably protected lacto-N-neotetraose tetrasaccharide structure was constructed through subsequential couplings with two thioglycoside donors, a glucosamine residue followed by a galactose derivative, using NIS/AgOTf as promoter. Removal of a silyl protecting group at the primary position of the non-reducing end residue afforded an acceptor to which the terminal α-galactosamine moiety was introduced using a 2-azido bromo sugar and halide assisted coupling conditions. Global deprotection afforded the non-phosphorylated target pentasaccharide, whereas removal of a silyl group from the primary position of the non-reducing end residue produced a free hydroxy group which was phosphorylated using H-phosphonate chemistry to yield the phosphoethanolamine-containing protected pentasaccharide. Partial deprotection afforded the phosphorylated target pentasaccharide with a free spacer amino group but with a protected phosphoethanolamino group. Conjugation of the spacer amino group to biotin or dimethyl squarate followed by deprotection of the phosphoethanolamino group and, in the case of the squarate derivative, further reaction with a protein then afforded the title conjugates.

  Conclusion: An effective synthesis of a biologically interesting pentasaccharide structure has been accomplished. The target pentasaccharide, an α-GalNAc substituted lacto-N-neotetraose structure, comprises a phosphoethanolamine motif and a spacer aglycon. Through the spacer, biotin and protein conjugates of the title compound have been constructed to allow further use in biological experiments.

  背景：在缺少O抗原多糖部分的细菌中，核心结构暴露在感染时免疫系统中，因此可以考虑和研究它们作为糖基共轭疫苗中的碳水化合物表面抗原。一种来自流感嗜血杆菌LPS的建议结构是磷酸化的五糖基6-PEtN-α-D-GalpNAc-(1→6)-β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp。 结果：从含间隔的乳糖衍生物开始，通过使用NIS/AgOTf作为促进剂，使用两个硫代糖苷供体（葡萄糖胺残基和半乳糖衍生物）进行连续耦合，构建了一个合适的保护的乳糖-N-新四糖四糖结构。去除非还原末端残基的硅保护基，得到一个受体，通过使用2-叠氮基溴糖和卤化物辅助耦合条件，引入了末端α-半乳糖胺基团。全局去保护后得到非磷酸化的目标五糖基，而从非还原末端残基中去除硅基团产生了一个自由的羟基，使用H-膦酸酯化学将其磷酸化，得到含磷酸乙醇胺的保护五糖基。部分去保护后得到含自由间隔氨基团但保护的磷酸乙醇胺基团的磷酸化目标五糖基。将间隔氨基团与生物素或二甲基方酸结合，去除磷酸乙醇胺基团并在二甲基方酸衍生物的情况下进一步与蛋白质反应，得到了标题共轭物。 结论：已成功合成了一种具有生物学意义的五糖基结构。目标五糖基是一种α-GalNAc取代的乳糖-N-新四糖结构，包括一个磷酸乙醇胺基团和一个间隔糖基。通过间隔糖基，构建了标题化合物的生物素和蛋白质共轭物，以便在生物实验中进一步使用。
• Chemical Synthesis of GM2 Glycans, Bioconjugation with Bacteriophage Qβ, and the Induction of Anticancer Antibodies
  作者：Zhaojun Yin、Steven Dulaney、Craig S. McKay、Claire Baniel、Katarzyna Kaczanowska、Sherif Ramadan、M. G. Finn、Xuefei Huang

  DOI：10.1002/cbic.201500499

  日期：2016.1

  Tumor‐associated carbohydrate antigens (TACAs) are attractive antitumor vaccine targets, due to their high expression levels in tumor cells. We focused on the synthesis of one TACA, ganglioside GM2, and showed that bacteriophage Qβ is a suitable platform to boost antibody responses toward GM2, emphasizing the potential of future GM2‐based vaccines.

  TACA 指出：肿瘤相关碳水化合物抗原 (TACA) 是有吸引力的抗肿瘤疫苗靶标，因为它们在肿瘤细胞中表达水平很高。我们专注于一种 TACA（神经节苷脂 GM2）的合成，并证明噬菌体 Qβ 是增强针对 GM2 的抗体反应的合适平台，强调了未来基于 GM2 的疫苗的潜力。
• A Stereoselective Approach for the Synthesis of α-Sialosides
  作者：Cristina De Meo、Alexei V. Demchenko、Geert-Jan Boons

  DOI：10.1021/jo010345f

  日期：2001.8.1

  A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.
• [EN] ANTI-GM1 ANTIBODY BINDING COMPOUNDS<br/>[FR] COMPOSÉS DE LIAISON À UN ANTICORPS ANTI-GM1
  申请人：[en]POLYNEURON PHARMACEUTICALS AG

  公开号：WO2022224035A2

  公开（公告）日：2022-10-27

  This disclosure provides glycan-conjugated compounds that specifically bind to anti -GM1 autoantibodies. These glycan-conjugated compounds can include a polymer backbone or support configured to display multiple glycan groups that are designed to mimic the natural GM1 epitope. The glycan-conjugated compounds can also be configured on a solid support. The linked glycan groups can be a novel analogue of the GM1 epitope. When several such glycan groups are configured on a polymeric backbone, the resulting compound provides for potent and specific binding to anti-GM1 IgG and IgM isotype autoantibodies in patient sera. This disclosure thus provides glycan-containing compounds of formula (I) that mimic the natural GM1 epitope, and therapeutically useful polymers that include a multitude of such ligands, designed to bind anti-GM1 antibodiesin vitrofor diagnostic use, and to sequester and eliminate anti-GM1 antibodiesin vivoor extracorporeal (ex vivo) for the treatment anti-GM1 autoantibody related neuropathies.