Extracurricular laboratory: Synthetic route of 23377-40-4

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 23377-40-4, 3-(Hexadecyloxy)propan-1-ol.

Synthetic Route of 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.

l-O-Hexadecyl^-deoxy-S-O-iS’^’-O-diacetyl^’-N-phthalimido-S’-azido-Z e’- dideoxy- -D-glucopyranosyl)-sn-glycerol (35)Compound 30 (0.4 mmol) and the previously reported lipid compound 34 (168 mg, 0.48mmol) were dissolved in anhydrous DCM (10 ml) under argon atmosphere. NIS (180 mg, 0.8 mmol) and silver triflate (20 mg, 0.08 mmol) were added. The reaction mixture was left under vigorous stirring for 3 hrs. At the completion of reaction (TLC monitoring), the reaction mixture was diluted by DCM (20 ml) and then filtered over Celite. The resulting organic layer was washed with saturated sodium thiosulphate solution (2 times), saturated sodium bicarbonate (3 times) and water (2 times). The organic layer was then dried over anhydrous Na2S04 and then concentrated under vacuum to give a brownish gel residue. The residue was then purified by flash chromatography (Hexane/Ethyl acetate, 4:6) to give compound 35 as a white solid. Yield 51%. (0265) 1H NMR (300 MHz, Chloroform-d) delta = 7.85 (dd, J=5.5, 3.1 , 2H, phthalimido aromatic protons), 7.73 (dd, J=5.5, 3.1 , 2H, phthalimido aromatic protons), 5.79 (dd, J=10.8, 9.0, 1 H, H-3), 5.38 (d, J=8.5, 1 H, H-1), 5.05 (dd, J=10.1 , 9.0, 1 H, H-4), 4.30 (dd, J=10.8, 8.5, H, H-2), 3.96 – 3.81 (m, 2H), 3.63 – 3.52 (m, 1 H), 3.43 (dt, J-13.6, 6.9, 1 H), 3.28 – 3.16 (m, 3H), 3.15 – 2.99 (m, 2H), 2.03 (s, 3H, Acetate CH3), 1.85 (s, 3H, Acetate CH3), 1.76 – 1.58 (m, 2H), 1.26 (s, 26H, Lipid tail), 0.89 (t, J = 6.6 Hz, 3H, lipid terminal -CH3).13C NMR (75 MHz, CDC13) delta = 170.12, 169.62, 134.27, 123.57, 97.99, 73.60, 71.82, 71.00, 70.53, 70.37, 67.04, 66.96, 54.68, 51.24, 31.91 , 29.73, 29.68, 29.59, 29.48, 29.34, 26.07, 22.67, 14.10.ES-MS: calcd: m/z: 723.4, found [M+Na]+ m/z: 723.5.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 23377-40-4, 3-(Hexadecyloxy)propan-1-ol.

Reference:
Patent; THE UNIVERSITY OF MANITOBA; OGUNSINA, Makanjuola; SAMADDER, Pranati; SCHWEIZER, Frank; ARTHUR, Gilbert; IDOWU, Temilolu; (119 pag.)WO2015/179983; (2015); A1;,
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