ethyl 2-trifluoroacetamido-1-thio-2-deoxy-β-D-glucopyranoside | 1429306-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-trifluoroacetamido-1-thio-2-deoxy-β-D-glucopyranoside
• 英文别名: TfaNH(-2d)Glc(b)-SEt；N-[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]-2,2,2-trifluoroacetamide
• CAS: 1429306-52-4
• 化学式: C₁₀H₁₆F₃NO₅S
• 分子量: 319.302
• InChiKey: FVITVZDEKXNTNP-PVFLNQBWSA-N

物化性质

• 沸点：
  508.5±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2-trifluoroacetamido-1-thio-2-deoxy-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 97.5h， 生成 6-O-(2-trifluoroacetamido-6-O-tert-butyldiphenylsilyl-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides

  摘要：

  Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the method with the formation of a pentasaccharide. The key building block is an orthogonally protected N-trifluoroacetamido thioglycoside donor that was added in succession to a glycosyl acceptor, enabling efficient glycosylation of the growing chain. In the second step of the iterative cycle, this building block is quantitatively deprotected at the C-6-hydroxyl position, ready for the next saccharide addition. Building from an azido-functionalised GlcNAc monosaccharide acceptor, the pentasaccharide was synthesised in seven steps in an overall yield of 25%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.01.008
• 作为产物：
  描述：

  ethyl 2-trifluoroacetamido-3,4,6-tri-O-acetyl-1-thio-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium 作用下， 反应 2.0h， 以100%的产率得到ethyl 2-trifluoroacetamido-1-thio-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides

  摘要：

  Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the method with the formation of a pentasaccharide. The key building block is an orthogonally protected N-trifluoroacetamido thioglycoside donor that was added in succession to a glycosyl acceptor, enabling efficient glycosylation of the growing chain. In the second step of the iterative cycle, this building block is quantitatively deprotected at the C-6-hydroxyl position, ready for the next saccharide addition. Building from an azido-functionalised GlcNAc monosaccharide acceptor, the pentasaccharide was synthesised in seven steps in an overall yield of 25%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.01.008

文献信息

• Chemoenzymatic Synthesis of <i>O</i>-Mannose Glycans Containing Sulfated or Nonsulfated HNK-1 Epitope
  作者：Tian Gao、Jingyu Yan、Chang-Cheng Liu、Angelina S. Palma、Zhimou Guo、Min Xiao、Xi Chen、Xinmiao Liang、Wengang Chai、Hongzhi Cao

  DOI：10.1021/jacs.9b08964

  日期：2019.12.11

  complex glycans with well-defined structures. Herein, we describe a highly efficient chemoenzymatic approach for the first col-lective synthesis of HNK-1-bearing O-mannose glycans with different branching patterns, and their non-sulfated counterparts. The successful strategy relies on both chemical glycosylation of a trisaccharide lactone donor for the in-troduction of sulfated HNK-1 branch, and on substrate

  人类自然杀伤-1 (HNK-1) 表位是一种独特的硫酸化三糖序列，存在于各种糖蛋白的 O-和 N-聚糖以及糖脂上。它在神经系统中过度表达，在神经再生、突触可塑性和神经元疾病中起着至关重要的作用。然而，由于无法获得具有明确结构的相关复杂聚糖，因此在分子水平上研究 HNK-1 在更复杂的聚糖环境中的功能作用仍然是一个巨大的挑战。在此，我们描述了一种高效的化学酶促方法，用于首次集体合成具有不同分支模式的 HNK-1 的 O-甘露糖聚糖及其非硫酸化对应物。成功的策略依赖于三糖内酯供体的化学糖基化以引入硫酸化 HNK-1 分支，以及细菌糖基转移酶的底物混杂性，这些酶可以耐受硫酸化底物以实现酶促多样化。对得到的复杂合成聚糖的聚糖微阵列分析证明它们被两种 HNK-1 特异性抗体识别，包括抗 HNK-1/N-CAM（CD57）和 Cat-315），这为识别表位提供了进一步的证据。这些抗体和硫酸盐基团在 HNK-1
• Chemoenzymatic synthesis of lacto-N-tetrasaccharide and sialyl lacto-N-tetrasaccharides
  作者：Wenlong Yao、Jun Yan、Xi Chen、Fengshan Wang、Hongzhi Cao

  DOI：10.1016/j.carres.2014.10.017

  日期：2015.1

  A concise and practical chemoenzymatic synthesis of lacto-N-tetraose, a major component and one of the most common core structures of human milk oligosaccharides (HMOs) was reported. This convergent synthesis relies on the glycosylation of a readily available lactoside acceptor with a lacto-N-biose donor generated from a highly efficient one-pot two-enzyme synthesis. (C) 2014 Elsevier Ltd. All rights reserved.