p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 501089-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: p-tolyl-3-O-benzyl-4,6-O-benzyledene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside；p-methylphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS: 501089-70-9
• 化学式: C₃₅H₃₁NO₆S
• 分子量: 593.7
• InChiKey: GAEITWYGENHSKM-VMGYOKIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 、 碳酸氢钠 、 乙二胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， 反应 17.5h， 生成 p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside
  参考文献：
  名称：

  Iterative one-pot syntheses of chitotetroses

  摘要：

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.007
• 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 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  一锅法合成大肠杆菌 O33 的 O 抗原四糖重复单元

  摘要：

  采用一锅糖基化策略合成了大肠杆菌 O33 的O抗原的四糖重复单元。四糖的成功合成对于研制针对大肠杆菌O33 的疫苗具有重要意义。

  DOI：

  10.1002/ejoc.202400464

文献信息

• A Four-Component One-Pot Synthesis of α-Gal Pentasaccharide
  作者：Yuhang Wang、Xuefei Huang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/ol0483246

  日期：2004.11.1

  A four-component one-pot sequential synthesis of alpha-Gal pentasaccharide 2 with minimal protecting group manipulations in a very short period of time is described in this paper. [structure: see text]

  本文介绍了一种四组分一锅法连续合成α-Gal五糖2的方法，该方法在非常短的时间内即可实现最少的保护基操作。[结构：见文字]
• One-Pot Glycosylation Strategy Assisted by Ion Mobility–Mass Spectrometry Analysis toward the Synthesis of <i>N</i>-Linked Oligosaccharides
  作者：Kalyana Kumar Ponnapalli、Yi-Chi Ho、Mei-Chun Tseng、Bhanu Vijaya Sekhar Vasamsetti、Jiun-Jie Shie

  DOI：10.1021/acs.joc.2c00184

  日期：2022.4.15

  for the synthesis of N-glycans are crucial for the rapid generation of pure samples to determine their biological functions. Herein, we describe a double one-pot strategy for the synthesis of N-glycans assisted by an IM–MS analysis approach for rapid screening of optimized glycosylation reaction conditions. This research includes triflate-mediated direct β-mannosylation and tandem glycosylation in a one-pot

  N-聚糖是几种细胞糖蛋白的主要成分。N-聚糖合成的一锅法对于快速生成纯样品以确定其生物学功能至关重要。在此，我们描述了一种通过 IM-MS 分析方法辅助合成N-聚糖的双一锅策略，用于快速筛选优化的糖基化反应条件。这项研究包括三氟甲磺酸酯介导的直接 β-甘露糖基化和串联糖基化，采用一锅法合成具有挑战性的N-连接三糖核心β-5。此外， N-连接三糖核心的一锅顺序糖基化7提供多种高甘露糖型N-聚糖，具有出色的立体选择性和区域选择性。特别是，应用离子淌度-质谱定量分析来确定粗反应混合物的立体选择性和区域选择性结果，以开发高效的一锅法。
• Chemoenzymatic synthesis of glycopeptides bearing rare N-glycan sequences with or without bisecting GlcNAc
  作者：Weizhun Yang、Sherif Ramadan、Jared Orwenyo、Tayeb Kakeshpour、Thomas Diaz、Yigitcan Eken、Miloslav Sanda、James E. Jackson、Angela K. Wilson、Xuefei Huang

  DOI：10.1039/c8sc02457j

  日期：——

  highly diverse structures in nature. Herein, we describe the first synthesis of rare multi-antennary N-glycan bearing glycan chains on 6-OH of both α1,6- and α1,3-linked mannose arms. To expedite divergent generation of N-glycan structures, four orthogonal protective groups were installed at the branching points on the core tetrasaccharide, which could be removed individually without affecting one another

  N-连接的糖肽在自然界中具有高度多样的结构。在这里，我们描述了α1,6-和α1,3-连接的甘露糖臂的6-OH上稀有的多天线N-聚糖带有聚糖链的首次合成。为了加快N-聚糖结构的发散生成，在核心四糖的分支点上安装了四个正交保护基团，这些基团可以单独除去而不会互相影响。另外，合成路线是灵活的，允许在合成的后期引入二等分的葡糖胺部分，进一步扩大了可实现的序列的多样性。二等分的氨基葡萄糖单元显着降低了相邻甘露糖的糖基化产率，这归因于基于分子模型分析的氨基葡萄糖所施加的空间位阻。关节杆菌内切-β - N-乙酰氨基葡糖苷酶（Endo-A）。根据供体的大小，Endo-A表现出有趣的底物偏好，这通过分子动力学研究得以合理化。这是首次合成具有二等分的N-乙酰基氨基葡萄糖（GlcNAc），稀有的N-聚糖分支和两个Lewis X三糖触角的糖肽，从而能够访问这类复杂的糖肽结构。
• Stereocontrolled Synthesis of <i>α</i>‐3‐Deoxy‐<scp>d</scp>‐manno‐oct‐2‐ulosonic Acid (<i>α</i>‐Kdo) Glycosides Using C3‐<i>p</i>‐Tolylthio‐Substituted Kdo Donors: Access to Highly Branched Kdo Oligosaccharides
  作者：Ao Sun、Zipeng Li、Yuchao Wang、Shuai Meng、Xiao Zhang、Xiangbao Meng、Shuchun Li、Zhongtang Li、Zhongjun Li

  DOI：10.1002/anie.202313985

  日期：2024.1.8

  glycosylation of 3-deoxy-d-manno-2-octulosonic acid (Kdo). The high reactivity and wide substrate scope of the donor enabled the synthesis of a range of Kdo-containing glycosides with complete α-stereoselectivity without the formation of 2,3-ene by-products. Several natural oligosaccharides were synthesized by a stepwise or one-pot process, including a highly branched Kdo pentasaccharide.

  已开发出一种用于 3-脱氧-d-甘露-2-辛糖酸 (Kdo) 糖基化的修饰供体。供体的高反应活性和广泛的底物范围使得能够合成一系列具有完全α-立体选择性的含Kdo糖苷，而不形成2,3-烯副产物。通过分步或一锅法合成了几种天然低聚糖，包括高度支化的 Kdo 五糖。
• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.