N-(4-{2-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-phenyl)-2,2,2-trifluoro-acetamide | 183239-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-{2-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-phenyl)-2,2,2-trifluoro-acetamide
• 英文别名: 2,2,2-trifluoro-N-[4-[2-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-phenylmethoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]phenyl]acetamide
• CAS: 183239-01-2
• 化学式: C₅₇H₆₀F₃NO₁₂
• 分子量: 1008.1
• InChiKey: VLVQKDJLUFMVPI-XMFQCKQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  73
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 N-(4-{2-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-phenyl)-2,2,2-trifluoro-acetamide 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以93%的产率得到N-(4-{2-[(2S,3R,4S,5R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-phenyl)-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of Moraxella catarrhalis

  摘要：

  The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-O-beta-D-glucopyranosyl-alpha-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the g-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates.

  DOI：

  10.1021/jo960789p
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 在 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 溶剂黄146 、 DMTST 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.83h， 生成 N-(4-{2-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-phenyl)-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of Moraxella catarrhalis

  摘要：

  The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-O-beta-D-glucopyranosyl-alpha-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the g-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates.

  DOI：

  10.1021/jo960789p

文献信息

• Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of <i>Moraxella catarrhalis</i>
  作者：Kerstin Ekelöf、Stefan Oscarson

  DOI：10.1021/jo960789p

  日期：1996.1.1

  The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-O-beta-D-glucopyranosyl-alpha-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the g-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates.