3-azidopropyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside | 819053-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-6-(3-azidopropoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 819053-52-6
• 化学式: C₃₀H₃₅N₃O₆
• 分子量: 533.624
• InChiKey: DORZPOGXDHOYIO-HBMYTODVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-azidopropyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 在 Lindlar's catalyst 三氟甲磺酸三甲基硅酯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 3-(N-tert-butyloxycarbonyl)aminopropyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Inhibition of Streptococcus suis Adhesion by Dendritic Galabiose Compounds at Low Nanomolar Concentration

  摘要：

  A series of mono-, di-, and tetravalent galablose (Ga1alpha1-4Gal) compounds were synthesized in good yields by coupling of a general carboxylic acid-bearing sugar building block to dendritic scaffolds based on the 3,5-di-(2-aminoethoxy)benzoic acid branching unit. Furthermore. a poly(amidoamine)- (PAMAM-) based dendritic galabioside was Synthesized containing eight galabiose units. All galabiosides were tested in a hemagglutination assay and a Surface plasmon resonance (SPR) competition assay in order to establish their potency in the binding to the bacterial Gram-positive pathogen Streptococcus suis. A monovalent cralabioside containing a short spacer was used as a reference compound in all the assays. Varations in the scaffold as well as in the spacer arms were introduced to determine their influence on the inhibition. The best inhibitor of hemagglutination was an octavalent galabioside with a minimal inhibitory concentration (MIC) of 0.3 nM, to the best of our knowledge the first, example of inhibition of bacterial binding by a soluble carbohydrate at a subnanomolar concentration.

  DOI：

  10.1021/jm049476+
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三乙基硅烷 、 sodium azide 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3-azidopropyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Inhibition of Streptococcus suis Adhesion by Dendritic Galabiose Compounds at Low Nanomolar Concentration

  摘要：

  A series of mono-, di-, and tetravalent galablose (Ga1alpha1-4Gal) compounds were synthesized in good yields by coupling of a general carboxylic acid-bearing sugar building block to dendritic scaffolds based on the 3,5-di-(2-aminoethoxy)benzoic acid branching unit. Furthermore. a poly(amidoamine)- (PAMAM-) based dendritic galabioside was Synthesized containing eight galabiose units. All galabiosides were tested in a hemagglutination assay and a Surface plasmon resonance (SPR) competition assay in order to establish their potency in the binding to the bacterial Gram-positive pathogen Streptococcus suis. A monovalent cralabioside containing a short spacer was used as a reference compound in all the assays. Varations in the scaffold as well as in the spacer arms were introduced to determine their influence on the inhibition. The best inhibitor of hemagglutination was an octavalent galabioside with a minimal inhibitory concentration (MIC) of 0.3 nM, to the best of our knowledge the first, example of inhibition of bacterial binding by a soluble carbohydrate at a subnanomolar concentration.

  DOI：

  10.1021/jm049476+

文献信息

• Synthesis of the pentasaccharide repeating unit of the <i>O</i>-antigen of <i>E. coli</i> O117:K98:H4
  作者：Pintu Kumar Mandal

  DOI：10.3762/bjoc.10.287

  日期：——

  O-antigen of E. coli O117:K98:H4 strain has been synthesized using a combination of sequential glycosylations and [3 + 2] block synthetic strategy from the suitably protected monosaccharide intermediates. Thioglycosides and glycosyl trichloroacetimidate derivatives have been used as glycosyl donors in the glycosylations.

  大肠杆菌O117：K98：H4菌株O抗原的五糖重复单元是使用顺序糖基化和[3 + 2]合成策略从适当保护的单糖中间体中合成的。硫代糖苷和糖基三氯乙酰亚氨酸酯衍生物已被用作糖基化中的糖基供体。
• Inhibition of <i>Streptococcus </i><i>s</i><i>uis</i> Adhesion by Dendritic Galabiose Compounds at Low Nanomolar Concentration
  作者：John A. F. Joosten、Vuokko Loimaranta、Chantal C. M. Appeldoorn、Sauli Haataja、Fatna Ait El Maate、Rob M. J. Liskamp、Jukka Finne、Roland J. Pieters

  DOI：10.1021/jm049476+

  日期：2004.12.1

  A series of mono-, di-, and tetravalent galablose (Ga1alpha1-4Gal) compounds were synthesized in good yields by coupling of a general carboxylic acid-bearing sugar building block to dendritic scaffolds based on the 3,5-di-(2-aminoethoxy)benzoic acid branching unit. Furthermore. a poly(amidoamine)- (PAMAM-) based dendritic galabioside was Synthesized containing eight galabiose units. All galabiosides were tested in a hemagglutination assay and a Surface plasmon resonance (SPR) competition assay in order to establish their potency in the binding to the bacterial Gram-positive pathogen Streptococcus suis. A monovalent cralabioside containing a short spacer was used as a reference compound in all the assays. Varations in the scaffold as well as in the spacer arms were introduced to determine their influence on the inhibition. The best inhibitor of hemagglutination was an octavalent galabioside with a minimal inhibitory concentration (MIC) of 0.3 nM, to the best of our knowledge the first, example of inhibition of bacterial binding by a soluble carbohydrate at a subnanomolar concentration.