2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranosyl azide | 51885-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranosyl azide
• CAS: 51885-53-1
• 化学式: C₁₂H₁₈N₄O₇
• 分子量: 330.298
• InChiKey: UASUEIULMRVEOJ-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  159.92
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 水 、 碘 、 乙酸酐 、 potassium bromide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 62.0h， 生成 1-(4-O-acetyl-2-deoxy-2-acetamido-β-D-glucuronopyranosyl)-4-phenyl[1,2,3]triazole
  参考文献：
  名称：

  Synthesis of N-(β-d-glycuronopyranosyl)alkanamides and 1-(β-d-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray crystallography

  摘要：

  The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important torsion angle is greatly influenced by substitutions in the sugar part. In the present work, uronic acid alkanamides and triazole derivatives have been designed and synthesized as newer analogs of N-glycoprotein linkage region to understand the influence of the carboxylic group on linkage region torsion as well as on molecular packing. Crystal structure of N-(beta-D-galacturonopyranosyl)acetamide is solved with the space group of P22(1)2(1). Comparison of the torsion angle and molecular packing of this compound with N-(beta-D-galactopyranosyl)acetamide showed that changing the C6-hydoxymethyl group to the carboxylic acid group has minimum influence on the N-glycosidic torsion angle, Phi(N) and significant influence on the molecular packing. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.023
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of N-(β-d-glycuronopyranosyl)alkanamides and 1-(β-d-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray crystallography

  摘要：

  The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important torsion angle is greatly influenced by substitutions in the sugar part. In the present work, uronic acid alkanamides and triazole derivatives have been designed and synthesized as newer analogs of N-glycoprotein linkage region to understand the influence of the carboxylic group on linkage region torsion as well as on molecular packing. Crystal structure of N-(beta-D-galacturonopyranosyl)acetamide is solved with the space group of P22(1)2(1). Comparison of the torsion angle and molecular packing of this compound with N-(beta-D-galactopyranosyl)acetamide showed that changing the C6-hydoxymethyl group to the carboxylic acid group has minimum influence on the N-glycosidic torsion angle, Phi(N) and significant influence on the molecular packing. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.023

文献信息

• The synthesis and ring-opening metathesis polymerization of glycomonomers
  作者：Lucy G. Weaver、Yogendra Singh、Paul L. Burn、Joanne T. Blanchfield

  DOI：10.1039/c5ra25732h

  日期：——

  The synthesis of a series of short poly(norbornene)s displaying pendant disaccharides is reported. para-(Propargyloxy)benzyl moieties were attached to a norbornenyl group via an ester or amide linkage, giving two different pre-monomers. A set of protected β-(1→6)-linked glucosamine-based disaccharides, structurally similar to the bacterial biofilm constituent poly-N-acetylglucosamine (PNAG), were attached

  报道了一系列显示侧链二糖的短聚降冰片烯的合成。对-（炔丙基氧基）苄基部分通过酯或酰胺键连接到降冰片烯基上，得到两种不同的前单体。在结构上类似于细菌生物膜成分聚-N-乙酰氨基葡萄糖（PNAG）的一组受保护的β-（1→6）-连接的基于氨基葡萄糖的二糖通过Huisgen 1,3-偶极环加成法连接到前单体上反应产生一系列“糖单体”。在格鲁布斯第三在新一代催化剂中，糖基单体显示出可变的反应性，这取决于降冰片烯基和苄基部分之间的键合类型（酯或酰胺）。通常，酰胺连接的糖单体的聚合速度比相应的酯连接的构建体慢得多，并且聚合度相对较低。所有材料均显示出相对窄的分子量分布（Đ = 1.2–1.5）。
• Stereoselective synthesis of glycosides and anomeric azides of glucosamine
  作者：Carlo Unverzagt、Horst Kunz

  DOI：10.1002/prac.19923340705

  日期：——

  The beta-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phase-transfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluoride was also revealed to be useful in the synthesis of beta-glucosamine glycosides and saccharides. Chitobiosyl azide 21 carrying a selectively removable 6-O-Mpm protection was synthesized from the O-acetyl protected N-phthaloyl glucosaminyl bromide and N-acetylglucosaminyl azide 13 as an acceptor selectively deblocked at O-4.