Adding a certain compound to certain chemical reactions, such as: 67853-03-6, Methyl 3-(hydroxymethyl)benzoate, 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, Quality Control of Methyl 3-(hydroxymethyl)benzoate, blongs to alcohols-buliding-blocks compound. Quality Control of Methyl 3-(hydroxymethyl)benzoate
Entry 27 Boron trifluoride etherate (25 muL, 0.20 mmol, 0.2 eq.) was added dropwise at -20C under argon to a stirred solution of 2,3,4,6-tetra-O-acetyl-alpha-d-galactopyranosyl trichloroacetimidate (1c) (500 mg, 1.01 mmol, 1 eq.) and methyl 3-hydroxymethylbenzoate (2d) (503 mg, 3.03 mmol, 3 eq.) in freshly distilled CH2Cl2 (8 mL). After 1 hour, Et3N (0.2 mL) was injected into the reaction mixture. Then, the solvent was evaporated, the residue was purified by silica gel column chromatography (PE:EtOAc, 5:1 to 3:1) to afford (1-methoxycarbonylphen-3-yl)methyl 2,3,4,6-tetra-O-acetyl-beta-d-galactoside (3e) as a white foam (397 mg, 79%). Rf = 0.27 (PE:EtOAc = 2:1); [alpha]D20 = -31.8 (c = 0.4, CH2Cl2); 1H NMR (400 MHz, CDCl3), delta (ppm): 7.94 (m, 2H, 2 HAr), 7.46 (d, J = 7.6 Hz, 1H, HAr), 7.40 (t, J = 8.0 Hz, 1H, HAr), 5.36 (d, J = 2.9 Hz, 1H, H4), 5.26 (dd, J = 10.4, 8.0 Hz, 1H, H2), 4.97 (dd, J = 10.5, 3.4 Hz, 1H, H3), 4.91 (d, J = 12.6 Hz, 1H, OCH2a), 4.65 (d, J = 12.6 Hz, 1H, OCH2b), 4.51 (d, J = 8.0 Hz, 1H, H1), 4.21-4.06 (m, 2H, H6), 3.91-3.85 (m, 4H, OMe, H5), 2.13 (s, 3H, COCH3), 2.03 (s, 3H, COCH3), 2.03 (s, 3H, COCH3), 1.95 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3), delta (ppm): 170.5 (C=O), 170.3 (C=O), 170.2 (C=O), 169.6 (C=O), 166.8 (COOMe), 137.3 (CAr), 132.2 (CAr-H), 130.4 (CAr), 129.2 (CAr-H), 128.70 (CAr-H), 128.65 (CAr-H), 100.0 (C1), 70.9 (C3), 70.8 (C5), 70.1 (OCH2), 68.8 (C2), 67.1 (C4), 61.3 (C6), 52.2 (OMe), 20.7 (3 × COCH3), 20.6 (COCH3); HRMS m/z: calcd. for C23H28NaO12, [M+Na]+ 519.1473, found 519.1466.
The synthetic route of 67853-03-6 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Wang, Shuai; Lafont, Dominique; Rahkila, Jani; Picod, Benjamin; Leino, Reko; Vidal, Sebastien; Carbohydrate Research; vol. 372; (2013); p. 35 – 46;,
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