With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33100-27-5,1,4,7,10,13-Pentaoxacyclopentadecane,as a common compound, the synthetic route is as follows.
[0083] (S) N-(Acetoxymethyl)-N-[(1R,2S,5R)-menthyloxycarbonyl]-4-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)homoalanine methyl ester (53): A solution of the aldehyde (40) (78 mg, 0.20 mmol) in dry dichloroethane (3 mL) wastreated with 1-aza-15-crown-5 (58 mg, 0.26 mmol) and triethylamine (38 mL, 0.27 mmol) and stirred for 10 min. at 26¡ãC. Then sodium (triacetoxy)borohydride (69 mg, 0.32 mmol) was added and the stirring continued for 2.5 h. After usualwork-up and concentration, the residue was purified by rotatory chromatography (hexane/EtOAc, 98:2), yielding theproduct (53) (108 mg, 91percent) as a yellowish slurry: [alpha]D =-51.22 (c 0.41, CHCl3); 1H NMR (500 MHz, CDCl3, 70 ¡ãC) deltaH0.77 (3H, d, J = 6.9 Hz, Me), 0.80-0.90 (1 H, m, 4?-Ha), 0.88 (3H, d, J = 7.3 Hz, Me), 0.89 (3H, d, J = 6.6 Hz, Me), 0.96(1 H, m, 6?-Hb), 1.05 (1 H, m, 3?-Ha), 1.36 (1 H, m, 2?-H), 1.55 (1 H, m, 5?-H), 1.62-1.69 (2H, m, 4?-Hb + 3?-Hb), 1.86 (1H, m, 2″-H), 1.96 (1 H, m, 3-Ha), 2.00 (3H, s, Ac), 2.02 (1 H, m, 6?-Ha), 2.23 (1 H, m, 3-Hb), 2.57-2.69 (2H, m, 4-H2),2.72-2.82 (4H, m, 2 x CH2N), 3.58-3.64 (16H, m, 8 x CH2O), 3.66 (3H, s, OMe), 4.52 (1 H, br b, 2-H), 4.60 (1 H, ddd, J= 4.4, 10.8, 11.0 Hz, 1?-H), 5.35 (1 H, br d, J = 11.0 Hz, OCHaN), 5.45 (1 H, d, J = 11.0 Hz, OCHbN); 13C NMR (125.7MHz, CDCl3, 70 ¡ãC) deltaC 16.3 (CH3), 20.7 (CH3), 21.8 (CH3), 23.6 (CH2), 25.9 (CH), 28.0 (CH2), 31.4 (CH), 34.3 (CH2),41.1 (CH2), 47.4 (CH), 51.9 (CH3), 53.0 (CH2), 54.7 (2 x CH2), 58.3 (CH), 69.8 (2 x CH2), 70.3 (2 x CH2), 70.6 (2 x CH2),71.1 (2 x CH2), 76.7 (CH), 155.3 (C), 170.3 (C), 171.7 (C); MS (EI) m/z (relative intensity) 588 (M+, 1), 545 (M+ – CHMe2, 2), 529 (M+ – OAc, 4), 232 ([1-methylen-1-aza-15-crown-5]+, 100. HRMS calcd for C29H52N2O10, 588.3622, found588.3626; calculated for C26H45N2O10, 545.3074, found 545.3077; calculated for C25H41N2O10, 529.2761, found529.2758; calculated for C11H22NO4, 232.1549, found 232.1542. Elemental analysis: Calculated for C29H52N2O10: C,59.16; H, 8.90; N, 4.76; found C, 59.24; H, 8.90; N, 4.88., 33100-27-5
33100-27-5 1,4,7,10,13-Pentaoxacyclopentadecane 36336, achiral-catalyst compound, is more and more widely used in various fields.
Reference£º
Patent; Consejo Superior De Investigaciones Cientificas (CSIC); ROMERO ESTUDILLO, Ivan Omar; BOTO CASTRO, Alicia; EP2957555; (2015); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare