(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid | 174713-20-3

• 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: (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid
• 英文别名: (2S,3R)-N-Boc-2-amino-4-benzyloxy-3-hydroxybuttersaeure；(2S,3R)-2-amino-4-benzyloxy-3-hydroxybuteric acid；(2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxybutanoic acid
• CAS: 174713-20-3
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: KWVMCWQUBBMVAY-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 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 17.5h， 生成 N-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-carbamoyl]-propyl}-succinamic acid
  参考文献：
  名称：

  作为唾液酸化的路易斯X模拟物的新型6-酰胺基-6-脱氧-1-半乳糖衍生物的合成。

  摘要：

  描述了几种唾液酸化的路易斯X（SLe（x））模拟物的合成和生物效能。这些模拟物结合了SLe（x）中存在的与E-选择素结合所必需的所有关键功能基团。由于2-，3-和4-羟基的相同排列，L-半乳糖用于模拟SLe（x）中天然存在的L-岩藻糖残基。几种合成和酶促制备的氨基酸用于模拟D-半乳糖残基。由于这些氨基酸合成中的可变性，研究了有效结合所必需的空间要求。引入带有羧酸盐的侧链作为唾液酸模拟物，并改变链长以最大化生物学活性。

  DOI：

  10.1016/s0968-0896(96)00236-2
• 作为产物：
  描述：

  苄氧基乙醛 生成 (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid
  参考文献：
  名称：

  Wu, Shih-Hsiung; Shimazaki, Makoto; Lin, Chun-Cheng, Angewandte Chemie, 1996, vol. 108, # 1, p. 106 - 108

  摘要：

  DOI：

文献信息

• Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides
  作者：Christoph M Huwe、Thomas J Woltering、Jan Jiricek、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1016/s0968-0896(98)00245-4

  日期：1999.5

  been developed as sialyl Lewis X mimetics. Although the compounds have a much simpler structure compared to SLe(x), up to 3-times higher binding affinity toward E-selectin and > 1000 times toward P-selectin was observed. Furthermore, a convenient strategy for generating a number of analogues from a SLe(x) mimetic template at a very late stage of the synthesis was introduced, using a ruthenium catalyzed

  已经开发了几种芳基取代的C-岩藻肽作为唾液酸化的路易斯X模拟物。尽管与SLe（x）相比，这些化合物的结构要简单得多，但观察到的对E-选择素的结合亲和力高达3倍，对P-选择素的结合亲和力高达1000倍。此外，介绍了在台式条件下使用钌催化的交叉烯烃复分解反应在合成的非常后期从SLe（x）模拟模板生成许多类似物的便捷策略。
• 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
• Cappi, Michael W.; Moree, Wilna J.; Qiao, Lei, Angewandte Chemie, 1996, vol. 108, # 20, p. 2501 - 2503
  作者：Cappi, Michael W.、Moree, Wilna J.、Qiao, Lei、Marron, Thomas G.、Weitz-Schmidt, Gabriele、Wong, Chi-Huey

  DOI：——

  日期：——
• C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity
  作者：Thomas J. Woltering、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1016/s0040-4039(96)02121-1

  日期：1996.12

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd
• FUCOPEPTIDES
  申请人：Novartis AG

  公开号：EP0815127A1

  公开（公告）日：1998-01-07