p-methoxyphenyl 3,6-di-O-benzyl-α-D-mannopyranoside | 123826-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,6-di-O-benzyl-α-D-mannopyranoside
• 英文别名: p-methoxyphenyl-3,6-O-dibenzyl-α-D-mannopyranoside
• CAS: 123826-52-8
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: OKWRMHZEVRPVMU-VKINHPFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.61
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,6-di-O-benzyl-α-D-mannopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  潜在的利什曼病碳水化合物疫苗的溶液和固相支持合成。

  摘要：

  描述了用于寄生虫利什曼病的潜在碳水化合物疫苗的合成。探索了新的溶液和固相合成策略，用于组装在利什曼原虫脂磷酸聚糖上发现的独特的四糖抗原。最初的溶液相合成依赖于硫糖苷作为结构单元，并通过氧化还原序列从乳清中建立了中心二糖。在解决方案和固体支持上都完成了第二种方法。固相合成依赖于单糖单元的组装，并用于评估有效安装半乳糖β-（1-4）甘露糖苷中的不同糖基化剂。事实证明，糖基磷酸酯最成功。利什曼原虫菌盖的第一次固相合成提供了以18％的总收率快速获得四糖的途径，而仅需一个纯化步骤。将合成的帽四糖与免疫刺激剂Pam3Cys结合以生成完全合成的碳水化合物疫苗1，并与载体蛋白KLH结合以形成半合成疫苗2。目前，这两种构建体均已在小鼠体内进行了初步免疫学实验，旨在开发针对寄生虫的疫苗疾病利什曼病。

  DOI：

  10.1021/jo015521z
• 作为产物：
  描述：

  p-methoxyphenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 三乙基硅烷 、 二正丁基氧化锡 、 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 1.0h， 生成 p-methoxyphenyl 3,6-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Efficient Convergent Synthesis of Bi-, Tri-, and Tetra-antennary Complex Type N-Glycans and Their HIV-1 Antigenicity

  摘要：

  The structural diversity of glycoproteins often comes from post-translational glycosylation with heterogeneous N-glycans. Understanding the complexity of glycans related to various biochemical processes demands a well-defined synthetic sugar library. We report herein a unified convergent strategy for the rapid production of bi-, tri-, and tetra-antennary complex type N-glycans with and without terminal N-acetylneuraminic acid residues connected via the alpha-2,6 or alpha-2,3 linkages. Moreover, using sialyltransferases to install sialic acid can minimize synthetic steps through the use of shared intermediates to simplify the complicated procedures associated with conventional sialic acid chemistry. Furthermore, these synthetic complex oligosaccharides were compiled to create a glycan array for the profiling of HIV-1 broadly neutralizing antibodies PG9 and PG16 that were isolated from HIV infected donors. From the study of antibody PG16, we identified potential natural and unnatural glycan ligands, which may facilitate the design of carbohydrate-based immunogens and hasten the HIV vaccine development.

  DOI：

  10.1021/ja409097c

文献信息

• A highly efficient and stereoselective cycloglycosylation. Synthesis of cyclo???→4)-[α-Man-(1→4)]5-α-Man-(1→???, a manno isomer of α-cyclodextrin
  作者：Masato Mori、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)72734-1

  日期：1989.1

  Stereocontrolled synthesis of a manno isomer of α-cyclodextrin was achieved for the first time employing PhSeOTf promoted cycloglycosylation of octadeca-O-benzyl-α-Man-(1→4)-???α-Man-(1→4)???4-α-Man-1→SMe.

  用PhSeOTf促进十八烷基-O-苄基-α-Man-（1→4）-α-Man-（1→4）的环糖基化反应，首次实现α-环糊精的甘露异构体的立体控制合成。 ?? 4 -α-Man-1→SMe。
• A highly stereoselective and practical synthesis of cyclomannohexaose, Cyclo{→4)-[α-d-Manp-(1→4)-]5-α-d-Manp-(1→}, a manno isomer of cyclomaltohexaose
  作者：Masato Mori、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0008-6215(89)85173-0

  日期：1989.10

  Phenylselenyl triflate-promoted cycloglycosylation of methyl O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→4) - [O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→4)]4-2,3,6-tri-O-benzyl-1-thio-α- d -mannopyranoside afforded 64% of cyclo→4)-[O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→4)]5-O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→} which was then hydrogenolysed to give a manno isomer of cyclomaltohexaose

  摘要苯基三氟甲苯磺酸酯促进甲基O-（2,3,6-tri-O-苄基-α-d-甘露吡喃糖基）-（1→4）-[O-（2,3,6-tri-O-苄基-α-d-甘露吡喃糖基）-（（1→4）] 4-2,3,6-三-O-苄基-1-硫代-α-d-甘露糖吡喃糖苷提供64％的环→4）-[O -（2,3,6-三-O-苄基-α-d-甘露吡喃糖基）-（（1→4）] 5-O-（2,3,6-三-O-苄基-α-d-甘露糖吡喃糖基） -（1→}然后水解得到环麦芽六糖（α-环糊精）的甘露糖异构体，以立体控制的方式由3,6-二-O-苄基-4-O-氯乙酰基制备了用于环糖基化的关键甘露糖基中间体-2-Op-甲基苯甲酰基-α-d-甘露吡喃糖基三氯乙酰亚胺酸酯和对甲氧基苯基3,6-二-O-苄基-2-Op-甲基苯甲酰基-α-d-甘露吡喃糖苷。
• METHODS FOR MODULAR SYNTHESIS OF N-GLYCANS AND ARRAYS THEREOF
  申请人：Academia Sinica

  公开号：US20170362265A1

  公开（公告）日：2017-12-21

  The present disclosure relates to novel modular methods for generating a diversity of N-glycans of high mannose, hybrid and complex types. The present disclosure also relates to exemplary arrays of the synthesized N-glycans spotted onto aluminium oxide coated slides. These arrays can be used to detect and analyze binding interactions between the synthesized N-glycans and glycan binding molecules, such as HIV-1 neutralizing antibodies. The present disclosure also relates to methods for identifying agents that bind to various types of molecules on the arrays and to defining the structural elements of the molecules on the arrays that bind to those agents. The arrays and methods provided herein may be used for general epitope identification, drug discovery and as analytical tools. The present disclosure also provides useful glycans and epitope determinants that are useful in detecting, diagnosing, recurrence monitoring and preventing pathological diseases such as HIV.

  本公开涉及一种用于生成高甘霖、杂交和复合型N-糖的新型模块化方法。本公开还涉及到合成的N-糖阵列被点在涂有氧化铝的载玻片上。这些阵列可用于检测和分析合成的N-糖与糖结合分子（如HIV-1中和抗体）之间的结合相互作用。本公开还涉及一种用于识别与阵列上各种类型分子结合的试剂和定义阵列上结合到这些试剂的分子的结构元素的方法。本文提供的阵列和方法可用于一般抗原表位鉴定、药物发现以及作为分析工具。本公开还提供了有用的糖类和表位决定因子，可用于检测、诊断、复发监测和预防HIV等病理性疾病。