(2S,3R,4S,5R,6R)-2-[(1R,2S,3R,4R,5R)-4-Azido-3-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | 162710-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-[(1R,2S,3R,4R,5R)-4-Azido-3-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• 英文别名: (2S,3R,4S,5R,6R)-2-[[(1R,2S,3R,4R,5R)-4-azido-3-[(4-methoxyphenyl)methoxy]-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 162710-60-3
• 化学式: C₂₀H₂₇N₃O₁₀
• 分子量: 469.448
• InChiKey: TZCGZPYWZJZULX-UVPAFCRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-[(1R,2S,3R,4R,5R)-4-Azido-3-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate N-甲基咪唑 、 3 A molecular sieve 、 4 A molecular sieve 、 水 、 氢气 、 sodium hydride 、 二正丁基氧化锡 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 mercury dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.75h， 生成 O-(2,3,4-Tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4)>-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharides Structurally Related to E-Selectin Ligands Are Inhibitors of Neural Cell Division: Synthesis, Conformational Analysis, and Biological Activity

  摘要：

  Oligosaccharides containing either the Lewis X trisaccharide fragment (3-fucosyl-N-acetyllactosamine) with N-acetylgalactosamine at the C-3 position of the galactose unit (compound 2 and the 1,6-anhydro derivative 5) or the trisaccharide 3-fucosyllactose having N-acetylneuraminic and sulfate groups at the C-3; position of the galactose (3 and 4, respectively) have been synthesized and tested for the ability to inhibit the division of astrocytes and transformed cell lines and their conformation studied. Compounds 3 and Care structurally related to sulfated Lewis X and sialyl Lewis X which are known to be recognized by E-selectin. The synthesis of 2 and 5 was accomplished by an original route starting from 1,6-anhydro-beta-D-mannose, while 3 and 4 were efficiently prepared from methyl beta-lactoside. The conformational analysis has been carried out using NMR, molecular mechanics, and molecular dynamics. Compounds 2-4 were inhibitors in all cell types tested showing ID50 values in the mu M range; however, 5 showed a marked decrease in the ID50 value on astrocytes emphasizing upon the importance of the relative orientation of the fucosyl unit. Tetrasaccharide 3 was the most active on astrocytes (ID50 = 35 mu M), whereas the sulfate 4 was the best inhibitor on tumor-forming C6 glioma cells (ID50 = 79 mu M).

  DOI：

  10.1021/jo00111a008
• 作为产物：
  描述：

  1,6-Anhydro-endo-2,3-O-(4-methoxybenzylidene)-β-D-mannopyranose 在 吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium methylate 、 sodium cyanoborohydride 、 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 61.17h， 生成 (2S,3R,4S,5R,6R)-2-[(1R,2S,3R,4R,5R)-4-Azido-3-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Oligosaccharides Structurally Related to E-Selectin Ligands Are Inhibitors of Neural Cell Division: Synthesis, Conformational Analysis, and Biological Activity

  摘要：

  Oligosaccharides containing either the Lewis X trisaccharide fragment (3-fucosyl-N-acetyllactosamine) with N-acetylgalactosamine at the C-3 position of the galactose unit (compound 2 and the 1,6-anhydro derivative 5) or the trisaccharide 3-fucosyllactose having N-acetylneuraminic and sulfate groups at the C-3; position of the galactose (3 and 4, respectively) have been synthesized and tested for the ability to inhibit the division of astrocytes and transformed cell lines and their conformation studied. Compounds 3 and Care structurally related to sulfated Lewis X and sialyl Lewis X which are known to be recognized by E-selectin. The synthesis of 2 and 5 was accomplished by an original route starting from 1,6-anhydro-beta-D-mannose, while 3 and 4 were efficiently prepared from methyl beta-lactoside. The conformational analysis has been carried out using NMR, molecular mechanics, and molecular dynamics. Compounds 2-4 were inhibitors in all cell types tested showing ID50 values in the mu M range; however, 5 showed a marked decrease in the ID50 value on astrocytes emphasizing upon the importance of the relative orientation of the fucosyl unit. Tetrasaccharide 3 was the most active on astrocytes (ID50 = 35 mu M), whereas the sulfate 4 was the best inhibitor on tumor-forming C6 glioma cells (ID50 = 79 mu M).

  DOI：

  10.1021/jo00111a008

文献信息

• Oligosaccharides Structurally Related to E-Selectin Ligands Are Inhibitors of Neural Cell Division: Synthesis, Conformational Analysis, and Biological Activity
  作者：Jose M. Coteron、Kamaljit Singh、Juan L. Asensio、Maria Dominguez-Dalda、Alfonso Fernandez-Mayoralas、Jesus Jimenez-Barbero、Manuel Martin-Lomas、Manuel Nieto-Sampedro

  DOI：10.1021/jo00111a008

  日期：1995.3

  Oligosaccharides containing either the Lewis X trisaccharide fragment (3-fucosyl-N-acetyllactosamine) with N-acetylgalactosamine at the C-3 position of the galactose unit (compound 2 and the 1,6-anhydro derivative 5) or the trisaccharide 3-fucosyllactose having N-acetylneuraminic and sulfate groups at the C-3; position of the galactose (3 and 4, respectively) have been synthesized and tested for the ability to inhibit the division of astrocytes and transformed cell lines and their conformation studied. Compounds 3 and Care structurally related to sulfated Lewis X and sialyl Lewis X which are known to be recognized by E-selectin. The synthesis of 2 and 5 was accomplished by an original route starting from 1,6-anhydro-beta-D-mannose, while 3 and 4 were efficiently prepared from methyl beta-lactoside. The conformational analysis has been carried out using NMR, molecular mechanics, and molecular dynamics. Compounds 2-4 were inhibitors in all cell types tested showing ID50 values in the mu M range; however, 5 showed a marked decrease in the ID50 value on astrocytes emphasizing upon the importance of the relative orientation of the fucosyl unit. Tetrasaccharide 3 was the most active on astrocytes (ID50 = 35 mu M), whereas the sulfate 4 was the best inhibitor on tumor-forming C6 glioma cells (ID50 = 79 mu M).