ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 168644-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 168644-99-3
• 化学式: C₃₇H₃₇NO₆S
• 分子量: 623.77
• InChiKey: BZAHNQRHULMHRM-VYGCBIOZSA-N

物化性质

• 沸点：
  743.6±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 molecular sieve 、 叠氮基三甲基硅烷 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

  摘要：

  Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The beta-mannosidic linkage was created by C-2 epimerization of the initially introduced beta-D-gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01540-8
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 4 A molecular sieve 、 sodium methylate 、 四氯化钛 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity

  摘要：

  通过对乙酰氨基-3-O-丙烯基-6-O-苄基-2-去氧-α-D-葡萄糖吡喃苷（7）的缩合反应，利用硫酸银盐催化的硫醚苷5和硫醚苷溴化物6在甲基三氟甲烷和溴化糖基6的存在下作为糖基供体，得到苄基-2-乙酰氨基-3-O-丙烯基-6-O-苄基-4-O-(3,4,6-三-O-苄基-2-去氧-2-邻苯二甲酰基-β-D-葡萄糖吡喃苷)-2-去氧-α-D-葡萄糖吡喃苷（8）。将其还原去邻苯二甲酰基，使用NaBH₄/醋酸作用得到苄基-2-乙酰氨基-3-O-丙烯基-4-O-(2-氨基-3,4,6-三-O-苄基-2-去氧-β-D-葡萄糖吡喃苷)-6-O-苄基-2-去氧-α-D-葡萄糖吡喃苷（11）。化合物11被N-酰化，得到苄基-2-乙酰氨基-4-O-(2-酰胺基-3,4,6-三-O-苄基-2-去氧-β-D-葡萄糖吡喃苷)-3-O-丙烯基-6-O-苄基-2-去氧-α-D-葡萄糖吡喃苷（12a）或（12b）。这些化合物被转化为相应的苄基-2-乙酰氨基-4-O-(2-酰胺基-3,4,6-三-O-苄基-2-去氧-β-D-葡萄糖吡喃苷)-6-O-苄基-3-O-羧甲基-2-去氧-α-D-葡萄糖吡喃苷，通过与H-L-Abu-D-isoGln(OBzl)缩合，接着氢解保护性苄基基团，得到糖肽16a和16b。描述了化合物8通过烷基保护基的内分子O→N迁移，随后与叠氮或叠氮醋酸盐反应还原为丙基残基，得到苄基-2-乙酰氨基-4-O-(3,4,6-三-O-苄基-2-去氧-2-丙基氨基-β-D-葡萄糖吡喃苷)-6-O-苄基-2-去氧-α-D-葡萄糖吡喃苷（9）。

  DOI：

  10.1135/cccc19980577

文献信息

• Synthesis of analogues of calicheamicin and neocarzinostatin chromophore
  作者：Alessandra Cirla、Angela R McHale、John Mann

  DOI：10.1016/j.tet.2004.03.021

  日期：2004.4

  The work presents a synthetic route to the CD ring of calicheamicin and in the case of neocarzinostatin an approach to a functionalised cyclopentane-1,3-diol containing the naturally occurring naphthoate and a glucosamine motif. In the case of the NCS derivative some biological activity (cytotoxicity) was observed.

  这项工作为加利车霉素的CD环提供了一条合成途径，在新carcarinostatin的情况下，提出了一种含有天然萘酚和葡糖胺基序的功能化环戊烷1,3-二醇的方法。在NCS衍生物的情况下，观察到一些生物学活性（细胞毒性）。
• Synthesis and Biological Activity of Tetrameric Ribitol Phosphate Fragments of <i>Staphylococcus aureus</i> Wall Teichoic Acid
  作者：Yoon-Chul Jung、Jae-Hyeok Lee、Sang Ah Kim、Timo Schmidt、Wonchul Lee、Bok Luel Lee、Hee-Seung Lee

  DOI：10.1021/acs.orglett.8b01725

  日期：2018.8.3

  A systematically designed and synthesized ribitol phosphate (RboP) oligomer using a series of building blocks, which make up the wall teichoic acid (WTA) of S. aureus, is presented. Based on the use of a solution-phase phosphodiester synthesis, a library of ribitol phosphate tetramers, decorated with d-alanine and N-acetylglucosamine (GlcNAc), were generated. The synthesized RboP tetramers showed increased

  提出了使用一系列构成模块的系统设计和合成的磷酸核糖醇磷酸酯（RboP）低聚物，该构成模块构成了金黄色葡萄球菌的壁骨壁酸（WTA）。基于使用溶液相磷酸二酯合成，生成了用d-丙氨酸和N-乙酰氨基葡糖（GlcNAc）修饰的核糖醇磷酸四聚体文库。在皮下气囊模型中，合成的RboP四聚体在小鼠中显示出增加的细胞因子水平。
• Polystyrylboronic acid as a reusable polymeric support for oligosaccharide synthesis
  作者：Gianluca Belogi、Tong Zhu、Geert-Jan Boons

  DOI：10.1016/s0040-4039(00)01184-9

  日期：2000.9

  Polystyrylboronic acid is an attractive polymeric support for oligosaccharide synthesis that can easily be prepared in high loading capacity and re-used after a synthetic sequence. Saccharides were loaded by heating in pyridine and released by treatment with a mixture of acetone and water. NIS/TMSOTf mediated glycosidations of thioglycosides gave a quantitative formation of disaccharides.

  聚苯乙烯基硼酸是用于寡糖合成的有吸引力的聚合物载体，其可以容易地以高负载量制备并在合成序列后重复使用。通过在吡啶中加热来装载糖，并通过用丙酮和水的混合物处理来释放糖。NIS / TMSOTf介导的硫糖苷的糖苷化定量形成了二糖。
• Synthesis of Linear and Branched Regioisomeric Chitooligosaccharides as Potential Mimetics of Natural Oligosaccharide Ligands of Natural Killer Cells NKR-P1 and CD69 Lectin Receptors
  作者：Anna Rohlenová、Miroslav Ledvina、David Šaman、Karel Bezouška

  DOI：10.1135/cccc20041781

  日期：——

  Regioisomer of chitobiose13with β(1→3) glycosidic bond and branched analog of chitotriose25having β(1→4) and β(1→3) glycosidic bonds, were prepared and tested as potential mimetics of natural oligosaccharide ligands for activating lectin receptors NKR-P1A and CD69 of natural killer (NK) cells. The structural requirements of NKR-P1 lectin receptor on effective mimetics of its natural ligands has been discussed. A significant binding activity of the branched trisaccharide25to the receptor CD69 was observed.

  制备了β(1→3)糖苷键的N-乙酰葡萄糖二聚体13的同分异构体和具有β(1→4)和β(1→3)糖苷键的分支寡糖25的类似物，作为天然寡糖配体激活自然杀伤细胞(NK细胞)的凝集素受体NKR-P1A和CD69的潜在模拟物进行测试。讨论了NKR-P1凝集素受体对其天然配体有效模拟物的结构要求。观察到分支三糖25与受体CD69的显著结合活性。
• Systematic synthesis of bisected <i>N</i>-glycans and unique recognitions by glycan-binding proteins
  作者：Xuefeng Cao、Shuaishuai Wang、Madhusudhan Reddy Gadi、Ding Liu、Peng G. Wang、Xiu-Feng Wan、Jian Zhang、Xi Chen、Lauren E. Pepi、Parastoo Azadi、Lei Li

  DOI：10.1039/d1sc05435j

  日期：——

  building blocks to afford two asymmetric bisecting “cores”. Subsequent enzymatic modular extension of the “cores” yielded a comprehensive library of biantennary N-glycans containing the bisecting GlcNAc and presenting 6 common glycan determinants in a combinatorial fashion. These bisected N-glycans and their non-bisected counterparts were used to construct a distinctive glycan microarray to study their

  二等分N-聚糖代表一类独特的蛋白质N-聚糖，在许多生物过程中起着关键作用。在此，我们描述了这些结构的系统合成。一分为二的N-聚糖六糖与连接在分支甘露糖残基 C2 处的两个正交保护基团进行化学组装，然后依次安装 GlcNAc 和 LacNAc 构建块以提供两个不对称的二等分“核心”。“核心”的后续酶促模块化延伸产生了一个全面的双触角N-聚糖库，其中包含平分的 GlcNAc 并以组合方式呈现 6 种常见的聚糖决定簇。这些平分N-聚糖及其未对分的对应物用于构建独特的聚糖微阵列，以研究它们被多种聚糖结合蛋白 (GBP) 识别，包括植物凝集素、动物凝集素和甲型流感病毒血凝素。值得注意的是，二等分 GlcNAc 可以赋予（PHA-L、rDCIR2）、增强（PHA-E）或消除（ConA、GNL、抗 CD15s 抗体等）特定 GBP 的 N-聚糖识别，并且被许多人耐受其他。总之，合成的化合物和独特的聚糖微