1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane | 181629-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane
• CAS: 181629-32-3
• 化学式: C₄₆H₅₇NO₁₀
• 分子量: 783.959
• InChiKey: BAVKHVKRSXVYSY-VRUMSENHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  57.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  131.01
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane 在 palladium on activated charcoal 盐酸 、 TEA 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 27.0h， 生成 (2S,3R)-2-(4-Carboxy-butyrylamino)-3,4-dihydroxy-butyric acid 3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-propyl ester
  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
• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基-Alpha-L-岩藻吡喃糖苷 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 双氧水 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 75.0h， 生成 1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane
  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