生命科学领域;制备:在1000 mL三口圆底烧瓶中,依次加入L-苏氨酸45 g(0.38 mol),无水甲醇(400mL),冰盐浴冷却,缓慢通入干燥的氯化氢气体(自制:采用浓硫酸、浓盐酸、氯化钠制备,经浓硫酸干燥),约4 h后固体完全消失,加热至回流反应3 h后,再次冷却,继续通入干燥氯化氢气体至饱和(称重至质量不变即为饱和),室温反应约3 d,TLC显示反应完全后,减压蒸尽溶剂,得L-苏氨酸甲酯盐酸盐68.5g。
生命科学
合成路线 1(1. 合成:39994-75-7)
- 步骤:将L-苏氨酸溶解在甲醇HCl溶液(2M)中并将反应混合物回流1小时。然后使用旋转蒸发器蒸发有机溶剂,并将同样的甲醛HCl溶液加入到反应混合物中并回流1小时。在反应时间之后,在减压下蒸发有机溶剂,得到白色固体化合物。
- 条件:Reflux(回流)
- 收率:98%
- 参考文献:[1] Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2851 - 2859 [2] Synthesis, 1999, # 10, p. 1739 - 1746 [3] Synthetic Communications, 2000, vol. 30, # 20, p. 3685 - 3691 [4] Bioorganic Chemistry, 2008, vol. 36, # 1, p. 4 - 15 [5] Synlett, 2009, # 8, p. 1227 - 1232 [6] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 3, p. 191 - 202 [7] Tetrahedron Asymmetry, 1996, vol. 7, # 1, p. 293 - 299 [8] Polymer, 2010, vol. 51, # 12, p. 2479 - 2485 [9] Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1536 - 1547 [10] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 14, p. 4775 - 4799 [11] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6273 - 6290 [12] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1764 - 1774 [13] Medicinal Chemistry Research, 2018, vol. 27, # 1, p. 285 - 307 [14] Organic and Biomolecular Chemistry, 2006, vol. 4, # 15, p. 2888 - 2897 [15] Tetrahedron, 2014, vol. 70, # 34, p. 5082 - 5092 [16] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944 [17] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 9899 - 9906 [18] Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10249 - 10258 [19] Synthetic Communications, 2010, vol. 40, # 8, p. 1161 - 1179 [20] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3850 - 3854 [21] Journal of Organic Chemistry, 1985, vol. 50, # 23, p. 4515 - 4523 [22] Angewandte Chemie, 1994, vol. 106, # 6, p. 693 - 695 [23] Tetrahedron Letters, 1995, vol. 36, # 4, p. 497 - 500 [24] Tetrahedron, 1997, vol. 53, # 18, p. 6473 - 6484 [25] Journal of Organic Chemistry, 1997, vol. 62, # 21, p. 7364 - 7375 [26] Tetrahedron, 1999, vol. 55, # 42, p. 12301 - 12308 [27] Patent: US2005/182262, 2005, A1. Location in patent: Page/Page column 2 [28] Chemistry - An Asian Journal, 2009, vol. 4, # 2, p. 328 - 335 [29] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 6, p. 2135 - 2140 [30] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1227 - 1236 [31] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9946 - 9957 [32] Journal of Natural Products, 2013, vol. 76, # 7, p. 1388 - 1391 [33] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 215 - 228 [34] Patent: CN106631900, 2017, A. Location in patent: Paragraph 0015 [35] Patent: CN106674254, 2017, A. Location in patent: Paragraph 0163-0167 [36] Journal of the American Chemical Society, 2017, vol. 139, # 38, p. 13420 - 13428