Adding a certain compound to certain chemical reactions, such as: 23377-40-4, 3-(Hexadecyloxy)propan-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, COA of Formula: C19H40O2, blongs to alcohols-buliding-blocks compound. COA of Formula: C19H40O2
Example 6 Hexadecyloxypropyl-2′,3′-isopropylideneuridin-5′-yl-vinyphosphonate TPSCl (5.54 g, 18.3 mmol) is added to the mixture of vinylphosphonic acid from the example 1 (1.8 g, 6.1 mmol), hexadecyloxypropanol (1.45 g, 3.05 mmol), and 1-methylimidazole (1.45 ml, 18.3 mmol) in DCM (60 ml). The reaction mixture is stirred overnight at rt, then extracted/washed with saturated solution of NaHCO3 (2 x 100 ml), 3% aqueous citric acid (2 x 100 ml) and dried over Na2SO4. The organic phase is concentrated in vacuo and the product is obtained by flash chromatography on silica gel using linear gradient of ethanol in chloroform in 71% yield (1.42 g, 2.16 mmol) in the form of colorless wax. A mixture of diastereoisomers ~ 1:1 1H NMR (500.0 MHz, CDCl3): 0.88 (m, 6H, CH3(CH2)15); 1.23-1.33 (m, 52H, CH3(CH2)13CH2CH2-O); 1.348, 1.352 (2 * q, 2 * 3H, 4J= 0.6, (CH3)2C); 1.54 (m, 4H, CH3(CH2)13CH2CH2O); 1.57 (s, 6H, (CH3)2C); 1.92, 1.94 (2 * p, 2 * 2H, Jvic = 6.1, OCH2CH2CH2OC16H33); 3.38, 3.39 (2 * t, 2 * 2H, Jvic, = 6.7, CH3(CH2)13CH2CH2O); 3.48, 3.49 (2 * t, 2 * 2H, Jvic = 6.1, OCH2CH2CH2OC16H33); 4.13, 4.15 (2 * td, 2 * 2H, Jvic = 6.1, JH,P = 4.8, OCH2CH2CH2OC16H33); 4.20-4.30 (m, 4H, H-5′); 4.34-4.38 (m, 2H, H-4′); 4.85, 4.86 (2 * dd, 2 * 1H, J3′,2′ = 6.5, J3′,4′ = 3.6, H-3′); 4.92 (dd, 2H, J2′,3′ = 6.5, J2′,1′ = 2.3, H-2′); 5.700, 5.704 (2 * d, 2 * 1H, J5,6 = 8.1 H-5); 5.74, 5.76 (2 * d, 2 * 1H, J1′,2′ = 2.3, H-1′); 6.03, 6.05 (2 * ddd, 2 * 1H, JH,P = 22.9, Jtrans = 18.4, Jcis = 12.7, =CHP); 6.16, 6.18 (2 * ddd, 2 * 1H, JH,P = 51.8, Jcis = 12.7, Jgem = 1.9, CHcisHtrans=CHP); 6.33, 6.35 (2 * ddd, 2 * 1H, JH,P = 25.5, Jtrans = 18.4, Jgem = 1.9, CHcisHtrans=CHP); 7.34, 7.39 (2 * d, 2 * 1H, J6,5 = 8.1, H-6). 13C NMR (125.7 MHz, CDCl3): 14.07 (CH3(CH2)15); 22.62 (CH3(CH2)13CH2CH2O); 25.19, 25.21 ((CH3)2C); 26.08 (CH3(CH2)14CH2O); 27.04, 27.06 ((CH3)2C); 29.29, 29.45, 29.55, 29.57, 29.58, 29.63 (CH3(CH2)14CH2O); 30.66, 30.68 (d, JC,P = 6.4, OCH2CH2CH2OC16H33); 31.85 (CH3(CH2)13CH2CH2O); 63.56 63.57 (d, JC,P = 5.5, OCH2CH2CH2OC16H33); 64.92, 65.01 (d, JC,P = 5.5, CH2-5′); 66.32, 66.36 (OCH2CH2CH2OC16H33); 71.15, 71.16 (CH3(CH2)14CH2O); 80.60, 80.67 (CH-3′); 84.44, 84.53 (CH-2′); 85.38, 85.62 (d, JC,P = 7.1, CH-4′); 93.82, 94.12 (CH-1′); 102.57, 102.64 (CH-5); 114.42, 114.46 (C(CH3)2); 124.75, 124.80 (d, JC,P = 184.0, =CHP); 136.75, 136.77 (d, JC,P = 1.9, CH2=CHP); 141.43, 141.48 (CH-6); 150.16 (C-2); 163.29, 163.32 (C-4). 31P NMR (202.3 MHz, CDCl3): 18.64, 18.80. IR vmax(KBr) 2925 (vs), 2854 (s), 1709 9vs, sh), 1696 (vs), 1630 (w), 1459 (m), 1421 (m), 1400 (w, sh), 1381 (m), 1270 (m, sh), 1250 (m, sh), 1109 (s), 1078 (s), 1028 (s), 1012 (s), 972 (m, sh), 859 (m), 762 (w), 548 (w), 514 (w) cm-1. HR-ESI C33H58O9N2P (M+H)+ calcd 657.3874; found 657.3876
The synthetic route of 23377-40-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Ustav Organicke Chemie A Biochemie Av Cr, V.v.i.; Mikrobiologicky Ustav AV CR V.V.I.; Ustav Molekularni Genetiky Av Cr, V.v.i.; Trios, spol. s r.o.; EP2527351; (2012); A1;,
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