2592-18-9 N-Boc-L-苏氨酸

中文名称: N-Boc-L-苏氨酸
英文名称: Boc-L-Threonine
CAS号
分子式: C₉H₁₇NO

名称和标识

中文名: N-Boc-L-苏氨酸
英文名: Boc-L-Threonine
CAS号: 2592-18-9
分子式: C9H17NO5
分子量: 219.24
中文别名: Boc-L-苏氨酸; N-(叔丁氧羰基)-L-苏氨酸; N-叔丁氧羰基-L-苏氨酸; 叔丁氧羰基-L-苏氨酸; 叔丁氧羰基L-苏氨酸; 腺氨; (2S,3R)-2-((叔丁氧羰基)氨基)-3-羟基丁酸; N-叔丁氧基羰基-L-苏氨酸

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生产及用途

用途与制备

作为氨基酸保护单体用于多肽合成；作为生化试剂；用于制备医药中间体及生物科技原料。

多肽合成；医药中间体；生物科技原料

合成路线 1（1. 合成：2592-18-9）

产率：99% 合成条件：With sodium hydrogencarbonate In methanol; water at 20℃; for 72 h; 实验步骤：制备52 N-Boc-L-苏氨酸向L-苏氨酸（400mg，3.36mmol）的MeOH（5mL）溶液中加入NaHCO₃（434mg，5.17mmol）的水（5mL）溶液，然后加入Boc₂O（1）得到0.07g，4.90mmol），并将反应在室温下搅拌3天。真空除去溶剂，残余物用水（20mL）稀释，用乙醚（2×20mL）洗涤。将水层用饱和NaHSO₃水溶液酸化，并用2-MeTHF萃取。将有机层用Na₂SO₄干燥并真空浓缩，得到标题化合物，为白色固体（730mg，99％）。1H NMR（400MHz，CDCl₃）：δppm1.24（d，3H），1.44（s，9H），4.26（d，1H），4.40（d，1H），5.52（d，1H），5.69（br s，1 H）。LCMS Rt = 1.68分钟MS m/z 218 [M + H] + 参考文献：[1] Patent: WO2013/114250, 2013, A1. Location in patent: Page/Page column 161; 162 [2] Patent: WO2013/110643, 2013, A1. Location in patent: Paragraph 00118; 00119 [3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1795 - 1802 [4] Patent: CN102993200, 2016, B. Location in patent: Paragraph 0043; 0044; 0045 [5] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5770 - 5781 [6] Patent: WO2014/120783, 2014, A1. Location in patent: Paragraph 0092 [7] Patent: WO2014/120786, 2014, A1. Location in patent: Paragraph 0100 [8] Patent: WO2017/201283, 2017, A1. Location in patent: Page/Page column 32 [9] Patent: WO2017/201285, 2017, A1. Location in patent: Page/Page column 26; 31; 33 [10] Patent: WO2018/26798, 2018, A1. Location in patent: Page/Page column 46; 50 [11] Patent: WO2018/26763, 2018, A1. Location in patent: Page/Page column 62-63 [12] Organic Syntheses, 1985, vol. 63, p. 160 - 160 [13] Angewandte Chemie - International Edition, 2014, vol. 53, # 11, p. 2964 - 2968 [14] Angew. Chem., 2014, vol. 126, # 11, p. 3008 - 3012,5 [15] Tetrahedron Asymmetry, 2017, vol. 28, # 12, p. 1675 - 1685 [16] Tetrahedron, 2012, vol. 68, # 2, p. 697 - 704 [17] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1489 - 1509 [18] Patent: WO2014/120800, 2014, A1. Location in patent: Paragraph 00108; page 39 [19] Patent: WO2018/26792, 2018, A1. Location in patent: Page/Page column 99 [20] Chemistry of Natural Compounds, 1979, vol. 15, p. 471 - 476 [21] Khimiya Prirodnykh Soedinenii, 1979, vol. 15, p. 543 - 548 [22] Journal of Organic Chemistry, 1982, vol. 47, # 26, p. 5160 - 5167 [23] Journal of Organic Chemistry, 1992, vol. 57, # 16, p. 4331 - 4333 [24] Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 5607 - 5618 [25] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 505 - 507 [26] Heterocycles, 2004, vol. 62, p. 869 - 876 [27] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4329 - 4332 [28] Chinese Chemical Letters, 2012, vol. 23, # 3, p. 297 - 300 [29] Journal of Medicinal Chemistry, 2012, vol. 55, # 10, p. 4824 - 4836 [30] Journal of the American Chemical Society, 2012, vol. 134, # 24, p. 10222 - 10227 [31] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 20, p. 6134 - 6143 [32] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 264 - 268 [33] Chemistry - A European Journal, 2013, vol. 19, # 22, p. 7020 - 7041 [34] Molecules, 2014, vol. 19, # 5, p. 6822 - 6837 [35] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4204 - 4219 [36] Patent: US2015/246907, 2015, A1. Location in patent: Paragraph 0134-0142 [37] Medicinal Chemistry Research, 2016, vol. 25, # 6, p. 1148 - 1162 [38] Patent: CN104592081, 2017, B. Location in patent: Paragraph 0013; 0029-0034