4-METHOXYPHENYLBETA-D-GALACTOPYRANOSIDE
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4-METHOXYPHENYLBETA-D-GALACTOPYRANOSIDE
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CAS No:
3150-20-7
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Formula:
C13H18O7
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Chemical Name:
4-METHOXYPHENYLBETA-D-GALACTOPYRANOSIDE
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Synonyms:
p-Methoxyphenyl?D-galactoside;p-Methoxyphenyl-beta-galactoside;p-Methoxyphenylgalactopyranoside;4-Methoxyphenylb-D-galactopyranoside;4-Methoxyphenylβ-D-Galactopyranoside;4-METHOXYPHENYLBETA-D-GALACTOPYRANOSIDE;4-Methoxyphenylbeta-D-galactopyranosidemin.98%
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CAS No:
4-METHOXYPHENYLBETA-D-GALACTOPYRANOSIDE Use and Manufacturing
Step 1: (2R, 3S, 4S, 5R, 6S) -2- ( ( (tert-Butyldimethylsilyl) oxy) methyl) -6- (4-methoxyphenoxy) tetrahydro-2H-pyran-3, 4, 5-triol (5a) To a solution of compound 19b (3.74 g, 13.1 mmol) , imidazole (1.96 g, 28.8 mmol) in DMF (30 mL) was added a solution of TBSCl (2.37 g, 15.7 mmol) in DMF (5 mL) dropwise at 0under a nitrogen atmosphere. After stirring at room temperature for 12 hrs, the reaction mixture was poured into water (100 mL) and extracted with EtOAc (2×30 mL) . The organic layer was evaporated and the crude product was purified by column chromatography (200300 mesh silica gel, eluted with EtOAc/PE 1:1) to afford compound 5a as a white solid (3.85 g, 74) :1H NMR (400 MHz, DMSO-d6) delta 6.98 (d, J 8.8 Hz, 2H) , 6.80 (d, J 8.8 Hz, 2H) , 5.30 (d, J 5.2 Hz, 1H) , 5.11 (d, J 4.8 Hz, 1H) , 5.06 (d, J 5.2 Hz, 1H) , 4.68 (d, J 7.6 Hz, 1H) , 3.88 (d, J 10.8 Hz, 1H) , 3.69 (s, 3H) , 3.65-3.58 (m, 1H) , 3.34-3.28 (m, 1H) , 3.25-3.16 (m, 2H) , 3.11-3.07 (m, 1H) , 0.85 (s, 9H) , 0.03 (s, 3H) , 0.01 (s, 3H) LC-MS (ESI) : 418.23 [M+NH4]+.
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