主要用于医药合成领域,作为手性中间体参与相关药物分子的构建。
医药
合成路线 1(1. 合成:23735-43-5)
产率:98%
合成条件:at 0 - 20℃;
实验步骤:根据制备(R) - ( - ) - 20a,(R) - ( - ) - 2,2-二甲基-4-(羟甲基)-1,3-二氧戊环(19b)所述的方法(2.50g) 得到右手(S) - (+) - 3-甲苯磺酰氧基-1,2-丙二醇丙酮化合物20b(5.23g,98%收率,99.2%ee)。 [α] D20 +4.5(c 1.0,EtOH)(点亮[α] D25 +4.7(c 1.0,EtOH))。26 IR,NMR和HRMS光谱的表征数据在各个方面与(R)相同 ) - ( - ) - 20a对映体。
参考文献:
- [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1719 - 1723 [2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213 [3] Tetrahedron, 2013, vol. 69, # 5, p. 1634 - 1648 [4] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6304 - 6311 [5] Journal of the Chemical Society, Chemical Communications, 1984, # 6, p. 349 - 350 [6] Magnetic Resonance in Chemistry, 1998, vol. 36, # 1, p. 64 - 68 [7] Patent: WO2016/94570, 2016, A1. Location in patent: Paragraph 00471 [8] Patent: WO2011/143497, 2011, A1. Location in patent: Page/Page column 50 [9] Tetrahedron: Asymmetry, 1995, vol. 6, # 5, p. 1181 - 1190 [10] European Journal of Organic Chemistry, 2006, # 21, p. 4805 - 4812 [11] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4415 - 4424 [12] Patent: US5182296, 1993, A [13] Chemistry and Biology, 2009, vol. 16, # 1, p. 82 - 92 [14] Patent: US6335366, 2002, B2. Location in patent: Referential example 6(1) [15] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6915 - 6919 [16] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3635 - 3649