化学合成。
化学合成
合成路线 1（1. 合成：31608-22-7）
产率：93%
合成条件：With toluene-4-sulfonic acid In diethyl ether at 0 - 20℃; for 3 h;
实验步骤：为了回流THF，在3.50小时内滴加（0.5L）48％HBr（358g，3.9mol）。将反应物再回流1.5小时，然后冷却，用[NAHCO 3]中和，用水分配，用盐水洗涤，并用[MGSO 4]干燥。得到1g，为无色液体。然后，通过注射器将二氢吡喃（31mL，339mmol）加入到冷却的[（0XB0; C）4-BROMOBUTANOL]（40g，261mmol）在200mL含有90mg [OFP-TOLUENESULFONIC]的无水醚中的溶液中。酸。在[0XB; C]下1小时和在室温下2小时后，将反应混合物用饱和碳酸氢钠溶液[（2×80）mL）和盐水（1×80mL）洗涤。有机层用无水[MGSO 4]干燥。过滤溶液，真空除去溶剂，得到57.4g（93％）产物，为无色油状物。标题化合物可如Grieco，P.A.，Larsen，S.D.，J。[ORG。 CHEM，] 51,3553-3555（1986）。 [NMR LH（CDCl 3）]：1.50-1。 65（m，4H），1.65-1。 90（m，4H），1.90-2。 10（m，2H），3.40-3.60（m，4H），3.75-3。 90（m，2H），4.55-4。 58（m，1H）。
参考文献：
- [1] European Journal of Organic Chemistry, 2002, # 17, p. 3024 - 3033 [2] Journal of Organic Chemistry, 1986, vol. 51, # 18, p. 3553 - 3555 [3] Journal of Organic Chemistry, 1993, vol. 58, # 22, p. 5964 - 5966 [4] Bulletin de la Societe Chimique de France, 1994, vol. 131, # 6, p. 699 - 705 [5] Patent: WO2004/4706, 2004, A1. Location in patent: Preparation 1 [6] Patent: WO2010/19511, 2010, A2. Location in patent: Page/Page column 93 [7] Patent: US2010/113333, 2010, A1 [8] Patent: US2011/263534, 2011, A1. Location in patent: Page/Page column 79 [9] Patent: US2008/287396, 2008, A1. Location in patent: Page/Page column 61-62 [10] Organic and Biomolecular Chemistry, 2005, vol. 3, # 15, p. 2824 - 2831 [11] Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 2, p. 413 - 425 [12] Tetrahedron Letters, 2013, vol. 54, # 18, p. 2231 - 2234 [13] Patent: EP2208720, 2010, A1. Location in patent: Page/Page column 17 [14] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4109 - 4118 [15] Tetrahedron Letters, 1995, vol. 36, # 1, p. 147 - 150 [16] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1728 - 1733 [17] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2032 - 2038 [18] Journal of Organic Chemistry, 1985, vol. 50, # 23, p. 4432 - 4439 [19] Tetrahedron Letters, 2011, vol. 52, # 7, p. 787 - 788 [20] Journal of Organic Chemistry, 1996, vol. 61, # 8, p. 2839 - 2844 [21] Journal of Labelled Compounds and Radiopharmaceuticals, 2010, vol. 53, # 5-6, p. 243 - 247 [22] Synthesis, 2005, # 6, p. 998 - 1004 [23] Patent: US2005/158239, 2005, A1. Location in patent: Page/Page column 15 [24] Patent: WO2008/81447, 2008, A2. Location in patent: Page/Page column 23-24 [25] Journal of Organic Chemistry, 1993, vol. 58, # 6, p. 1458 - 1465 [26] Journal of Chemical Research, Miniprint, 1984, # 11, p. 3131 - 3149 [27] Russian Journal of Organic Chemistry, 1994, vol. 30, # 11.1, p. 1729 - 1734 [28] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 11, p. 1644 - 1649 [29] Phosphorus, Sulfur and Silicon and Related Elements, 2001, vol. 171-172, p. 167 - 172 [30] Patent: US2003/17278, 2003, A1 [31] Patent: US2003/17278, 2003, A1 [32] Patent: US3983155, 1976, A [33] Patent: US3993687, 1976, A [34] Patent: US3981880, 1976, A [35] Patent: US3987083, 1976, A [36] Patent: US3983153, 1976, A [37] Patent: US3983154, 1976, A [38] Patent: US2005/192263, 2005, A1. Location in patent: Page/Page column 35 [39] Organic and Biomolecular Chemistry, 2013, vol. 11, # 6, p. 881 - 885 [40] Patent: WO2014/117090, 2014, A1. Location in patent: Page/Page column 106 [41] Lipids, 2015, vol. 50, # 10, p. 1043 - 1050 [42] Langmuir, 2016, vol. 32, # 14, p. 3340 - 3347 [43] Patent: US3959346, 1976, A [44] Patent: US4008263, 1977, A [45] Patent: US3980691, 1976, A
