methyl 2,3,4-tri-O-benzoyl-6-O-chloracetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside | 1073182-16-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-O-chloracetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(2S,4aR,6S,7R,8R,8aR)-7-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4,5-dibenzoyloxy-2-[(2-chloroacetyl)oxymethyl]oxan-3-yl] benzoate
• CAS: 1073182-16-7
• 化学式: C₄₃H₄₀ClN₃O₁₄
• 分子量: 858.255
• InChiKey: RSCARXIJLOPXJG-AKALQYQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-chloracetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 aluminum (III) chloride 、 硼烷-三甲胺络合物 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以76%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-beta-D-glucopyranosyl-(1->3)-2-azido-6-O-benzyl-2-deoxy-alpha-D-galactopyranoside
  参考文献：
  名称：

  First Synthesis of Pentasaccharide Glycoform I of the Outer Core Region of the Pseudomonas aeruginosa Lipopolysaccharide

  摘要：

  The synthesis of a pentasaccharide representing the glycoform 1, which is one of two naturally Occurring glycoforms of the outer core of Pseudomonas aeruginosa lipopolysaccharide, and its analogues, differing in the N-substituent in the galactosamine unit, is reported. The main features of the synthetic scheme included the assembly of the pentasaccharide backbone by successive introduction of monosaccharide units, the use of glucosyl donors with specific location of acyl protecting groups capable of the remote anchimeric participation for highly stereoselective alpha-glucosylation, and efficient reduction of the azido group allowing high-yielding transformation of the intermediary azido pentasaccharide into final products.

  DOI：

  10.1021/jo801561p
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-benzoyl-6-O-chloracetyl-1-thio-β-D-glucopyranoside 、 methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 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， 反应 2.5h， 以75%的产率得到methyl 2,3,4-tri-O-benzoyl-6-O-chloracetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  First Synthesis of Pentasaccharide Glycoform I of the Outer Core Region of the Pseudomonas aeruginosa Lipopolysaccharide

  摘要：

  The synthesis of a pentasaccharide representing the glycoform 1, which is one of two naturally Occurring glycoforms of the outer core of Pseudomonas aeruginosa lipopolysaccharide, and its analogues, differing in the N-substituent in the galactosamine unit, is reported. The main features of the synthetic scheme included the assembly of the pentasaccharide backbone by successive introduction of monosaccharide units, the use of glucosyl donors with specific location of acyl protecting groups capable of the remote anchimeric participation for highly stereoselective alpha-glucosylation, and efficient reduction of the azido group allowing high-yielding transformation of the intermediary azido pentasaccharide into final products.

  DOI：

  10.1021/jo801561p

文献信息

• First Synthesis of Pentasaccharide Glycoform I of the Outer Core Region of the <i>Pseudomonas aeruginosa</i> Lipopolysaccharide
  作者：Bozhena S. Komarova、Yury E. Tsvetkov、Gerald B. Pier、Nikolay E. Nifantiev

  DOI：10.1021/jo801561p

  日期：2008.11.7

  The synthesis of a pentasaccharide representing the glycoform 1, which is one of two naturally Occurring glycoforms of the outer core of Pseudomonas aeruginosa lipopolysaccharide, and its analogues, differing in the N-substituent in the galactosamine unit, is reported. The main features of the synthetic scheme included the assembly of the pentasaccharide backbone by successive introduction of monosaccharide units, the use of glucosyl donors with specific location of acyl protecting groups capable of the remote anchimeric participation for highly stereoselective alpha-glucosylation, and efficient reduction of the azido group allowing high-yielding transformation of the intermediary azido pentasaccharide into final products.