[(3S,4S,5R)-6-[(4aR,6S,7R,8R,8aS)-7-acetamido-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]hexyl] methanesulfonate | 192065-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: [(3S,4S,5R)-6-[(4aR,6S,7R,8R,8aS)-7-acetamido-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]hexyl] methanesulfonate
• CAS: 192065-22-8
• 化学式: C₅₉H₈₃NO₁₄SSi
• 分子量: 1090.46
• InChiKey: DJFLHOHUKYODQU-WJWPCHODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.26
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(3S,4S,5R)-6-[(4aR,6S,7R,8R,8aS)-7-acetamido-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]hexyl] methanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以76%的产率得到N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide
  参考文献：
  名称：

  Synthesis of 12 Stereochemically and Structurally Diverse C-Trisaccharides

  摘要：

  Cell surface carbohydrates and their analogs may be used to study the cellular interactions responsible for adhesion to pathogenic bacteria, viruses, and other cells and may represent leads for drug discovery. We have generated 12 C-trisaccharides (7-18) as potential inhibitors for the cell surface proteins of the bacterium Helicobactor pylori. The strategy used has resulted in the generation of C-trisaccharides structures that are represented by the formula Fuc-alpha(1-2)-hexose-(1-3)-GlcNAc where each of the 12 compounds possesses a central sugar that has been systematically replaced with stereochemically diverse structures, including D and L sugars, through de novo synthesis. This approach relies upon an organometallic coupling of terminal monosaccharides 19 and 20 to prepare a ''disaccharide'' in a convergent manner. This intermediate is then divergently derivatized to form a variety of structural analogs about the central hexose. For the separable compounds, the assignment of stereochemistry was done using standard NMR techniques. In cases where inseparable diastereomeric mixtures were generated, we have described a novel recursive stereochemical deconvolution strategy. This recursive strategy is demonstrated in the diastereoselective synthesis of trisaccharides 14, subsequent to its initial rapid synthesis as a component of a diastereomeric mixture. Biological assays of these compounds should provide an insight into the binding requirements of carbohydrate receptors.

  DOI：

  10.1021/jo9621534
• 作为产物：
  描述：

  N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-but-3-enyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide 在 吡啶 、 sodium tetrahydroborate 、 锂硼氢 、 9-borabicyclo[3.3.1]nonane dimer 、 phosphate buffer 、 乙醇 、 双氧水 、 戴斯-马丁氧化剂 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.76h， 生成 [(3S,4S,5R)-6-[(4aR,6S,7R,8R,8aS)-7-acetamido-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]hexyl] methanesulfonate
  参考文献：
  名称：

  Synthesis of 12 Stereochemically and Structurally Diverse C-Trisaccharides

  摘要：

  Cell surface carbohydrates and their analogs may be used to study the cellular interactions responsible for adhesion to pathogenic bacteria, viruses, and other cells and may represent leads for drug discovery. We have generated 12 C-trisaccharides (7-18) as potential inhibitors for the cell surface proteins of the bacterium Helicobactor pylori. The strategy used has resulted in the generation of C-trisaccharides structures that are represented by the formula Fuc-alpha(1-2)-hexose-(1-3)-GlcNAc where each of the 12 compounds possesses a central sugar that has been systematically replaced with stereochemically diverse structures, including D and L sugars, through de novo synthesis. This approach relies upon an organometallic coupling of terminal monosaccharides 19 and 20 to prepare a ''disaccharide'' in a convergent manner. This intermediate is then divergently derivatized to form a variety of structural analogs about the central hexose. For the separable compounds, the assignment of stereochemistry was done using standard NMR techniques. In cases where inseparable diastereomeric mixtures were generated, we have described a novel recursive stereochemical deconvolution strategy. This recursive strategy is demonstrated in the diastereoselective synthesis of trisaccharides 14, subsequent to its initial rapid synthesis as a component of a diastereomeric mixture. Biological assays of these compounds should provide an insight into the binding requirements of carbohydrate receptors.

  DOI：

  10.1021/jo9621534

文献信息

• Synthesis of 12 Stereochemically and Structurally Diverse C-Trisaccharides
  作者：Daniel P. Sutherlin、Robert W. Armstrong

  DOI：10.1021/jo9621534

  日期：1997.8.1

  Cell surface carbohydrates and their analogs may be used to study the cellular interactions responsible for adhesion to pathogenic bacteria, viruses, and other cells and may represent leads for drug discovery. We have generated 12 C-trisaccharides (7-18) as potential inhibitors for the cell surface proteins of the bacterium Helicobactor pylori. The strategy used has resulted in the generation of C-trisaccharides structures that are represented by the formula Fuc-alpha(1-2)-hexose-(1-3)-GlcNAc where each of the 12 compounds possesses a central sugar that has been systematically replaced with stereochemically diverse structures, including D and L sugars, through de novo synthesis. This approach relies upon an organometallic coupling of terminal monosaccharides 19 and 20 to prepare a ''disaccharide'' in a convergent manner. This intermediate is then divergently derivatized to form a variety of structural analogs about the central hexose. For the separable compounds, the assignment of stereochemistry was done using standard NMR techniques. In cases where inseparable diastereomeric mixtures were generated, we have described a novel recursive stereochemical deconvolution strategy. This recursive strategy is demonstrated in the diastereoselective synthesis of trisaccharides 14, subsequent to its initial rapid synthesis as a component of a diastereomeric mixture. Biological assays of these compounds should provide an insight into the binding requirements of carbohydrate receptors.