(Z)-1-(3-carboxylmethylene-β-D-galactopyranosyl)-4-(α-L-fucopyranosyl)-2-butene | 163732-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-(3-carboxylmethylene-β-D-galactopyranosyl)-4-(α-L-fucopyranosyl)-2-butene
• 英文别名: 2-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(Z)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]but-2-enyl]oxan-4-yl]oxyacetic acid
• CAS: 163732-13-6
• 化学式: C₁₈H₃₀O₁₁
• 分子量: 422.43
• InChiKey: PQVSXMNRJPSTTH-ZCYFTROPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (Z)-1-(3-carboxylmethylene-β-D-galactopyranosyl)-4-(α-L-fucopyranosyl)-2-butene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到1-(3-carboxylmethylene-β-D-galactopyranosyl)-4-(α-L-fucopyranosyl)butane
  参考文献：
  名称：

  Design and Synthesis of Sialyl Lewis X Mimetics

  摘要：

  DOI：

  10.1021/ja00124a037
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium hydroxide 、 Amberlite IR 400 (OH-) resin 、 sodium hexamethyldisilazane 、 乙酸酐 、 四丁基碘化铵 、 二正丁基氧化锡 、 对甲苯磺酸 、 臭氧 、 溶剂黄146 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 (Z)-1-(3-carboxylmethylene-β-D-galactopyranosyl)-4-(α-L-fucopyranosyl)-2-butene
  参考文献：
  名称：

  Design and synthesis of C-linked fucosides as inhibitors of E-selectin

  摘要：

  Two series of C-linked fucosides as mimetics for the tetrasaccharide sialyl Lewis X have been synthesized and tested as inhibitors of E-Selectin. The fucopeptides have been prepared from three key intermediates, including alpha-C-allyl fucose, natural and unnatural amino acids bearing hydroxyl groups and an alpha,omega-diacid moiety for the imitation of the essential three parts of SLe(x), i.e., the Fuc, Gal, and NeuAc. The nature and distance of the linkage of the fucose moiety to the amino acids as well as the distance between the amino acids and the terminal carboxylic acid group turned out to be crucial for the biological activity. In addition the necessity of both OH groups (4- and 6-OH) in the Gal part could be confirmed. Conformational NMR study of the most active mimetic supports the structure-activity relationship. A second series of mimetics was prepared, where Fuc and Gal moieties were purely C-linked. In the synthesis of beta-C-allyl galactose an intramolecular 1,2-hydride shift led to an interesting side product. However, the substituted glycosidic oxygens led to a substantial loss of conformational constrain, which could not be compensated and resulted in low activity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00127-7

文献信息

• Design and Synthesis of Sialyl Lewis X Mimetics
  作者：Taketo Uchiyama、Vassil P. Vassilev、Tetsuya Kajimoto、Weichyun Wong、Chun-Cheng Lin、Hongmei Huang、Chi-Huey Wong

  DOI：10.1021/ja00124a037

  日期：1995.5
• Design and synthesis of C-linked fucosides as inhibitors of E-selectin
  作者：Taketo Uchiyama、Thomas J. Woltering、Weichyun Wong、Chun-Cheng Lin、Tetsuya Kajimoto、Maki Takebayashi、Gabriel Wéitz-Schmidt、Tetsuo Asakura、Masatoshi Noda、Chi-Huey Wong

  DOI：10.1016/0968-0896(96)00127-7

  日期：1996.7

  Two series of C-linked fucosides as mimetics for the tetrasaccharide sialyl Lewis X have been synthesized and tested as inhibitors of E-Selectin. The fucopeptides have been prepared from three key intermediates, including alpha-C-allyl fucose, natural and unnatural amino acids bearing hydroxyl groups and an alpha,omega-diacid moiety for the imitation of the essential three parts of SLe(x), i.e., the Fuc, Gal, and NeuAc. The nature and distance of the linkage of the fucose moiety to the amino acids as well as the distance between the amino acids and the terminal carboxylic acid group turned out to be crucial for the biological activity. In addition the necessity of both OH groups (4- and 6-OH) in the Gal part could be confirmed. Conformational NMR study of the most active mimetic supports the structure-activity relationship. A second series of mimetics was prepared, where Fuc and Gal moieties were purely C-linked. In the synthesis of beta-C-allyl galactose an intramolecular 1,2-hydride shift led to an interesting side product. However, the substituted glycosidic oxygens led to a substantial loss of conformational constrain, which could not be compensated and resulted in low activity. Copyright (C) 1996 Elsevier Science Ltd