Category: 23377-40-4

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 23377-40-4, name is 3-(Hexadecyloxy)propan-1-ol, molecular formula is C19H40O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 23377-40-4

S13: A suspension of 3-hexadecyloxypropan-l-ol (1.58 g, 5.26 mmol) and DIPEA (0.92 mL, 5.26 mmol) in anhydrous acetonitrile (25 mL) was treated dropwise over a 10 min period with 3-((chloro(diisopropylamino)phosphino)oxy)-propanenitrile (1.2 mL, 5.26 mmol). After 18 h at rt, the mixture was quenched with sat. aq. NaHC03 (15 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic phases were concentrated by rotary evaporation, and flash chromatography (column volume 25 mm x 140 mm, 10 to 20% gradient of EtOAc in hexanes) provided S13 (1.40 g, 53%) as a white solid: 1H NMR (400 MHz, CDC13) delta 3.89 – 3.54 (m, 6H), 3.49 (t, 7= 6.3 Hz, 2H), 3.39 (t, 7= 6.7 Hz, 2H), 2.64 (t, J = 6.6 Hz, 2H), 1.87 (p, J = 6.3 Hz, 2H), 1.57 (p, J = 6.3 Hz, 2H), 1.25 (s, 26H), 1.18 (dd, J = 6.8, 3.5 Hz, 12H), 0.87 (t, J= 6.6 Hz, 3H); 31P NMR (162 MHz, CDC13) delta 147.40.

With the rapid development of chemical substances, we look forward to future research findings about 23377-40-4.

Reference:
Patent; EMORY UNIVERSITY; PAINTER, George, R.; GUTHRIE, David, B.; BLUEMLING, Gregory, R.; NATCHUS, Michael, R.; (179 pag.)WO2017/156380; (2017); A1;,
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Synthetic Route of 23377-40-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 23377-40-4 as follows.

9-(5-Phosphono-pent-2-en-l-yl)-adenine mono-(3-hexadecyloxy-l- propyl) phosphonoester (16)A solution of compound 13 (0.12Og, 0.424 mmol), 3-hexadecyloxy- propan-1-ol (HDPOH) (0.191g, 0.64 mmol) and DMAP (0.078g, 0.64 mmol) in DMF (10 mL) was treated with DCC (0.262g, 1.26 mmol) at room temperature. The reaction mixture was warmed up to 8O0C and stirred for overnight. After concentration, the residue was purified with a gradient mixture of chloroform, methanol, ammonia water and water (80:20:1 :1 to 100:40:3:3) by silica gel column chromatography to give 0.065g of product 16 (0.115 mmol, 27% yield); 1H NMR (MeOH-^) 58.21 (s, IH), 8.19 (s, IH) 5.84-5.74 (m, IH), 5.65-5.57 (m, IH), 4.92 (d, J = 7.0 Hz, 2H), 3.94 (q, J = 6.2 Hz, 2H), 3.52 (t, J = 6.2 Hz, 2H), 3.37 (t, J = 6.6 Hz, 2H), 2.58-2.44 (m, 2H), 1.90-1.78 (m, 2H), 1.74-1.62 (m, 2H), 1.54-1.43 (m, 2H), 1.36-1.14 (m, 12H), 0.89 (t, J = 7.0 Hz, 3H); 31P NMR (MeOH-^) 525.89; MS (ESI) m/z 566 (M+H)+, 564 (M-HV.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERISITY OF CALIFORNIA; WO2006/137953; (2006); A1;,
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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, 23377-40-4, blongs to alcohols-buliding-blocks compound. 23377-40-4

3-(Hexadecyloxy)propan-1-ol was synthesized in one step according to the method ofYamano, Y. et al., Biorg. Med. Chem. (2012) 20:3658-3665 and recrystallized from hexane. The crystalline product (200mg, 0.67mmol) was dissolved in dry CH2C12 and diisopropylethylamine (0.70 mL, 2.68 mmol, 4 equiv) was added while stirring at RT. 2- Cyanoethyloxy(N,N-diisopropylamino) phosphonamidic chloride (0. l8mL, 0.8mmol, 1.2 eq) was added dropwise and the solution was stirred for 45mm. After completion lSmL of CH2C12 were added and the organic phase was washed with saturated aqueous NaHCO3 anddried over MgSO4. The crude product was purified on a silica column with Hex:EtOAc:NEt350:50:1 as eluent to afford the title compound as a colorless liquid (175mg, 52% yield). Rf inEtOAc =0.28. MS (ESI): found 501 (M+H); mass expected for (C28H57N203P + H = 501.4).?H NMR (400 MHz, CDC13) 0.89 (t, J=6.85 Hz, 3H, CH3CH2) 1.19 (dd, J=6.72, 3.42 Hz,12H, 2 (CH3)2CHN) 1.26 (s, 26 H, 13 (Cl2)11) 1.56 (quin, J=6.94 Hz, 2H, OCH2CH2CH2)1.88 (quin, J=6.30 Hz, 2H, POCH2CH2CH2O) 2.64 (t, J6.60 Hz, 2H, CH2CN) 3.40 (t,J=6.66 Hz, 2H, OC1j2CH2CH2) 3.50 (t, J=6.30 Hz, 2H, POCH2CH2CLLaO) 3.54 – 3.65 (m,2H, 2 CH) 3.65 – 3.79 (m, 2H, POC1j2CH2CH2O) 3.79 – 3.93 ppm (m, 2H, POCH2CH2CN).?3C NMR (101 MHz, CDC13) oe 14.1 (s, 1C, CH3CH2) 20.3 (d, J6.60 Hz, 1C, CH2CN) 22.7(s, 1C, CH2CH2CH3) 24.5 and 24.63 (2 d, J=7.70 Hz, 2x2C, (CH3)2CHN) 26.2 (s, 1C,OCH2CH2CH2) 29.3 (s, 1CH211) 29.5 (s, 1CH211) 29.6 (s, 2CH211) 29.6 (s, 1CH211) 29.7 (s,5CH211) 29.8 (s, 1CH211) 31.5 (d,J7.34 Hz, 1C, POCH2CH2CH2O) 31.9 (s, 1CH211) 43.0 (d,J=1 1.74 Hz, 2C, 2 CH) 58.3 (d, J=19.07 Hz, 1C, POCH2CH2CN) 60.7 (d, J17.61 Hz, 1C,POCH2CH2CH2O) 67.3 (s, 1C, POCH2CH2CH2O) 71.1 (s, 1C, OCH2CH2CH2), 117.6 ppm (s,1C, CN). 3?P NMR (162 MHz, CDC13, ?H-decoupled) 8 147.56 ppm (s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.

Reference:
Patent; UNIVERSITY OF MASSACHUSETTS; UNIVERSITY OF SOUTHAMPTON; WATTS, Jonathan; HAITCHI, Hans, Michael; PENDERGRAFF, Hannah; (88 pag.)WO2018/226788; (2018); A1;,
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