3-(benzyloxycarbonylamino)propyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 932015-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzyloxycarbonylamino)propyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-4-benzoyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)-6-[3-(phenylmethoxycarbonylamino)propoxy]oxan-3-yl] benzoate
• CAS: 932015-08-2
• 化学式: C₃₉H₃₆N₂O₁₁
• 分子量: 708.722
• InChiKey: APWGEJNMLYBWOU-VPWIBOAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonylamino)propyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 ethyl 6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→6)-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  四-β-（1→6）-d-葡萄糖胺及相关四糖分子内环化的立体化学：构象立体控制和邻近基团参与的作用

  摘要：

  反应条件，离去基团的性质以及糖基化单糖中C-2处的取代基对线性四-β-（1→6）-d-葡糖胺和某些“混合”环化的立体化学结果的影响已经检查了包含葡萄糖和葡糖胺残基的四糖。甲苯和腈溶剂提高了环化反应的β-立体选择性，但是，在这些溶剂中形成环状产物的总效率低于在二氯甲烷中的效率。使用溴化物或戊烯基糖苷代替硫糖苷作为离去基团不会增加β-立体选择性。用N-Troc取代糖基化单元中的N-邻苯二甲酰基不会影响环化的立体选择性，而四糖 发现含有2-O-苯甲酰基葡萄糖而不是葡糖胺作为糖基供体部分的糖专门提供β-连接的环状产物。利用该发现，已经有效地合成了具有两个葡萄糖和两个葡萄糖胺单元的交替或相邻排列的两个环状四糖。这些循环旨在用于制备具有不同配体取向的二价糖簇。葡萄糖和氨基葡萄糖前体环化的立体选择性差异是由O-苯甲酰基与N-Phth和N-Troc对应物的更有效的邻位参与所引起的，这通过计算稳定能和周围的

  DOI：

  10.1016/j.carres.2012.12.005
• 作为产物：
  描述：

  (2R,3S,4R,5R)-2-(acetoxymethyl)-6-bromo-5-(1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyran-3,4-diyl dibenzoate 在 甲醇 、 氰化汞 、 乙酰氯 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 3-(benzyloxycarbonylamino)propyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  The study of the reaction of terminated oligomerization in the synthesis of oligo-(β1-6)-glucosamines

  摘要：

  The applicability of terminated oligomerization to the synthesis of oligo-(beta 1-6)-glucosamines, fragments of the intercellular polysaccharide adhesin of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and spacered mono- and disaccharides as terminating molecules were also attempted. The primary formation of cyclic products of monomer intramolecular glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approximately 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligoglucosamines with a high molecular mass.

  DOI：

  10.1134/s1068162006040108

文献信息

• Methods for inhibiting biofilm formation
  申请人：ONEBIOPHARMA INC.

  公开号：US10828360B1

  公开（公告）日：2020-11-10

  Disclosed are methods and kits of parts useful in inhibiting biofilm formation in vivo in subjects at risk of developing biofilms. These methods include inhibiting biofilm formation where the extracellular matrix in the biofilm includes poly-β-(1→6)glucosamine structures.

  本文披露了一种用于抑制易于形成生物膜的方法和配件套件，适用于处于发展生物膜风险中的受试者体内。这些方法包括在生物膜中抑制生物膜形成，其中生物膜的细胞外基质包括聚β-(1→6)葡聚糖结构。
• [EN] METHODS FOR PROVIDING CONTINUOUS THERAPY AGAINST PNAG COMPRISING MICROBES<br/>[FR] PROCÉDÉS POUR FOURNIR UNE THÉRAPIE CONTINUE CONTRE DES MICROBES CONTENANT PNAG
  申请人：ONEBIOPHARMA INC

  公开号：WO2021102320A1

  公开（公告）日：2021-05-27

  Disclosed are antimicrobial vaccines comprising oligosaccharide β-(1→6)-glucosamine groups.

  披露了包含寡糖β-(1→6)-葡萄糖胺基团的抗微生物疫苗。
• [EN] LOW CONTAMINANT ANTIMICROBIAL VACCINES<br/>[FR] VACCINS ANTIMICROBIENS À FAIBLE TENEUR EN CONTAMINANTS
  申请人：ONEBIOPHARMA INC

  公开号：WO2021096921A1

  公开（公告）日：2021-05-20

  Disclosed are antimicrobial vaccines comprising oligosaccharide β-(1→6)-glucosamine groups.

  披露了包含寡糖β-(1→6)-葡萄糖胺基团的抗微生物疫苗。
• [EN] ANTIMICROBIAL VACCINE COMPOSITIONS<br/>[FR] COMPOSITIONS DE VACCINS ANTIMICROBIENS
  申请人：ONEBIOPHARMA INC

  公开号：WO2021041721A8

  公开（公告）日：2021-05-14
• Synthesis of five nona-β-(1→6)-d-glucosamines with various patterns of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus
  作者：Olga N. Yudina、Marina L. Gening、Yury E. Tsvetkov、Alexey A. Grachev、Gerald B. Pier、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2011.02.018

  日期：2011.5

  A series of five 3-acetamidopropyl beta-glycosides of nona-beta-(1 -> 6)-glucosamines containing two N-acetyl-glucosamine residues separated by a different number of glucosamine units with free amino groups have been synthesized using a convergent blockwise approach. Oxazoline glycosylation was used to introduce N-acetylglucosamine residues. These nonasaccharides are structurally related to the poly-N-acetylglucosamine (PNAG) extracellular polysaccharide of Staphylococcus aureus and can be used as models for biochemical and immunological studies. (C) 2011 Elsevier Ltd. All rights reserved.