methyl 3-deoxy-3-(2-naphthamido)-2-O-p-toluoyl-β-D-talopyranoside | 1346535-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-deoxy-3-(2-naphthamido)-2-O-p-toluoyl-β-D-talopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-methoxy-4-(naphthalene-2-carbonylamino)oxan-3-yl] 4-methylbenzoate
• CAS: 1346535-79-2
• 化学式: C₂₆H₂₇NO₇
• 分子量: 465.503
• InChiKey: SPGJSEPZEKLCPQ-PTMVLBRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-deoxy-3-(2-naphthamido)-2-O-p-toluoyl-β-D-talopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 1.5h， 以94%的产率得到methyl 3-deoxy-3-(2-naphthamido)-β-D-talopyranoside
  参考文献：
  名称：

  Synthesis of 3-amido-3-deoxy-β-d-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors

  摘要：

  3-Deoxy-3-amino-beta-D-talopyranosides have been synthesized for the first time. The amines were obtained from galactopyranosides through 2,3-anhydrogulosides that were opened to idosides followed by an oxidation/reductive amination sequence. From the amines, 11 corresponding 3-deoxy-3-arylamido-beta-talopyranosides have been synthesized and evaluated as inhibitors against galectin-1, -2, -3, -4C, -4N, -7, -8N and -9N. The synthesized talosamides showed selectivity for Galectin-4C with three of the mono-saccharides having dissociation constants at around 100 mu M against the lectin, which is more than two orders of magnitude better than methyl beta-galactoside and significantly better than the previous best galectin-4C monosaccharide inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.098
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-β-D-idopyranoside 在 吡啶 、 ammonium acetate 、 水 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 methyl 3-deoxy-3-(2-naphthamido)-2-O-p-toluoyl-β-D-talopyranoside
  参考文献：
  名称：

  Synthesis of 3-amido-3-deoxy-β-d-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors

  摘要：

  3-Deoxy-3-amino-beta-D-talopyranosides have been synthesized for the first time. The amines were obtained from galactopyranosides through 2,3-anhydrogulosides that were opened to idosides followed by an oxidation/reductive amination sequence. From the amines, 11 corresponding 3-deoxy-3-arylamido-beta-talopyranosides have been synthesized and evaluated as inhibitors against galectin-1, -2, -3, -4C, -4N, -7, -8N and -9N. The synthesized talosamides showed selectivity for Galectin-4C with three of the mono-saccharides having dissociation constants at around 100 mu M against the lectin, which is more than two orders of magnitude better than methyl beta-galactoside and significantly better than the previous best galectin-4C monosaccharide inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.098

文献信息

• Synthesis of 3-amido-3-deoxy-β-d-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors
  作者：Christopher T. Öberg、Ann-Louise Noresson、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.tet.2011.09.098

  日期：2011.11

  3-Deoxy-3-amino-beta-D-talopyranosides have been synthesized for the first time. The amines were obtained from galactopyranosides through 2,3-anhydrogulosides that were opened to idosides followed by an oxidation/reductive amination sequence. From the amines, 11 corresponding 3-deoxy-3-arylamido-beta-talopyranosides have been synthesized and evaluated as inhibitors against galectin-1, -2, -3, -4C, -4N, -7, -8N and -9N. The synthesized talosamides showed selectivity for Galectin-4C with three of the mono-saccharides having dissociation constants at around 100 mu M against the lectin, which is more than two orders of magnitude better than methyl beta-galactoside and significantly better than the previous best galectin-4C monosaccharide inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.