allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl-(1→4)-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranoside | 1215016-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl-(1→4)-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-azido-5-[(4-methoxyphenyl)methoxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(phenylmethoxymethyl)-2-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 1215016-57-1
• 化学式: C₄₆H₅₄N₄O₁₁
• 分子量: 838.955
• InChiKey: DGEXENOOHUDILK-RGIBRDSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl-(1→4)-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranoside 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium hydride 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 56.75h， 生成 allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-[(R)-1'-(D-glutamyl-L-alanylamido)carboxyethyl]-6-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Partially N-Acetylated Chitooligosaccharides and Muropeptides

  摘要：

  Partially N-acetylated chitooligosaccharides and muropeptides are referred to as microbial associated molecular patterns (MAMPs). To shed light on the molecular basis of their recognition by the innate immunity system of living organisms, their production in pure form is necessary. To this end, we present here the first synthetic strategy for the obtainment of a series of partially N-acetylated muropeptides as well as of a chitodisaccharide and a chitotetrasaccharide, all possessing a well-defined N-acetylation pattern.

  DOI：

  10.1055/s-0033-1340323
• 作为产物：
  描述：

  C₂₇H₃₀Cl₃NO₉ 在 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl-(1→4)-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Partially N-Acetylated Chitooligosaccharides and Muropeptides

  摘要：

  Partially N-acetylated chitooligosaccharides and muropeptides are referred to as microbial associated molecular patterns (MAMPs). To shed light on the molecular basis of their recognition by the innate immunity system of living organisms, their production in pure form is necessary. To this end, we present here the first synthetic strategy for the obtainment of a series of partially N-acetylated muropeptides as well as of a chitodisaccharide and a chitotetrasaccharide, all possessing a well-defined N-acetylation pattern.

  DOI：

  10.1055/s-0033-1340323

文献信息

• Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments
  作者：Luigi Cirillo、Emiliano Bedini、Antonio Molinaro、Michelangelo Parrilli

  DOI：10.1016/j.tetlet.2009.12.124

  日期：2010.2

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.