2-萘基甲基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷 | 190181-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-萘基甲基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷
• 中文别名: 2-萘基甲基2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷
• 英文名称: (2-naphthyl)methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-Naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(naphthalen-2-ylmethoxy)oxan-2-yl]methyl acetate
• CAS: 190181-66-9
• 化学式: C₂₅H₂₉NO₉
• 分子量: 487.507
• InChiKey: ATDNOJRGVAVGOC-FXEFVXDJSA-N

物化性质

• 沸点：
  656.8±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-萘基甲基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷 在 硫酸 、 sodium methylate 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.08h， 生成 (R)-2-[(4aR,6R,7R,8R,8aS)-7-Acetylamino-6-(naphthalen-2-ylmethoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid
  参考文献：
  名称：

  Synthesis of hydrophobic derivatives of muramyldipeptides

  摘要：

  DOI：

  10.1007/bf02273926
• 作为产物：
  描述：

  2-萘甲醇 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 3 A molecular sieve 、 mercury(II) iodide 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到2-萘基甲基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷
  参考文献：
  名称：

  Synthesis of hydrophobic derivatives of muramyldipeptides

  摘要：

  DOI：

  10.1007/bf02273926

文献信息

• Zemlyakov; Kur'yanov; Sidorova, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 551 - 558
  作者：Zemlyakov、Kur'yanov、Sidorova、Chirva

  DOI：——

  日期：——
• Synthesis of?-glycosides of n-acetylglucosamine in the presence of HgI2
  作者：A. E. Zemlyakov、V. O. Kur'yanov、V. Ya. Chirva

  DOI：10.1007/bf01372338

  日期：1996.5
• Thioglycosides Are Efficient Metabolic Decoys of Glycosylation that Reduce Selectin Dependent Leukocyte Adhesion
  作者：Shuen-Shiuan Wang、Xuefeng Gao、Virginia del Solar、Xinheng Yu、Aristotelis Antonopoulos、Alan E. Friedman、Eryn K. Matich、G. Ekin Atilla-Gokcumen、Mehrab Nasirikenari、Joseph T. Lau、Anne Dell、Stuart M. Haslam、Roger A. Laine、Khushi L. Matta、Sriram Neelamegham

  DOI：10.1016/j.chembiol.2018.09.012

  日期：2018.12

  Metabolic decoys are synthetic analogs of naturally occurring biosynthetic acceptors. These compounds divert cellular biosynthetic pathways by acting as artificial substrates that usurp the activity of natural enzymes. While O-linked glycosides are common, they are only partially effective even at millimolar concentrations. In contrast, we report that N-acetylglucosamine (GlcNAc) incorporated into various thioglycosides robustly truncate cell surface N- and O-linked glycan biosynthesis at 10-100 mu M concentrations. The > 10-fold greater inhibition is in part due to the resistance of thioglycosides to hydrolysis by intracellular hexosaminidases. The thioglycosides reduce beta-galactose incorporation into lactosamine chains, cell surface sialyl Lewis-X expression, and leukocyte rolling on selectin substrates including inflamed endothelial cells under fluid shear. Treatment of granulocytes with thioglycosides prior to infusion into mouse inhibited neutrophil homing to sites of acute inflammation and bone marrow by similar to 80%-90%. Overall, thioglycosides represent an easy to synthesize class of efficient metabolic inhibitors or decoys. They reduce N-/O-linked glycan biosynthesis and inflammatory leukocyte accumulation.
• Synthesis of hydrophobic derivatives of muramyldipeptides
  作者：A. E. Zemlyakov、V. O. Kur'yanov、V. V. Tsikalov、E. A. Aksenova、V. Ya. Chirva

  DOI：10.1007/bf02273926

  日期：1997.1
• Synthesis and glycan priming activity of acetylated disaccharides
  作者：Arun K Sarkar、Jillian R Brown、Jeffrey D Esko

  DOI：10.1016/s0008-6215(00)00200-7

  日期：2000.11

  Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-beta -D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O -acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O -acetyl-beta -D-galactopyranoside (14), 2-naphthylmethy12,3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside oside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2-acetamido-4, 6-di-O -acetyl-2-deoxy-or-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd. All rights reserved.