D-Glucopyranoside, methyl 1-C-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]- synthesis
- Product Name:D-Glucopyranoside, methyl 1-C-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]-
- CAS Number:912917-83-0
- Molecular formula:C20H23ClO7
- Molecular Weight:410.85
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![Silane,[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy](1,1-diMethylethyl)diMethyl-](/CAS/20150408/GIF/864070-19-9.gif)
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Yield:912917-83-0 84.8%
Reaction Conditions:
Stage #1: [4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silanewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;Inert atmosphere;
Stage #2: D-Glucono-1,5-lactone in tetrahydrofuran;hexane;toluene at -78; for 1.5 h;Inert atmosphere;
Stage #3: methanolwith methanesulfonic acid in tetrahydrofuran;hexane;toluene at 20; for 18 h;Inert atmosphere;
Steps:
7 Synthesis of (3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (7)
56.36 g (0.13 mol) at -78 °C 6 is added to 300 mL of tetrahydrofuran under nitrogen protection In a solution, 2.3 mL (0.18 mol) of n-butyl hexane solution was slowly added dropwise to the mixture. After stirring the reaction for 30 min, the reaction droplets were added to the pre-cooling under the protection of nitrogen. -78 ° C 3 (80.10g, 0.18mol) in toluene solution, stirring reaction for 1.5h, then adding methanesulfonic acid in methanol solution (250mL, 0.6mol / L), Slowly rise to room temperature and react for 18 h. Quench the reaction by adding 65 mL of saturated sodium bicarbonate solution. The organic layer was combined and dried over anhydrous sodium sulfate. 7 crude product was obtained, dissolved in hot toluene solution, slowly added to hexane solution, and a yellow solid was precipitated, 77.8 g, yield 84.8%.
References:
CN108285439,2018,A Location in patent:Paragraph 0038; 0109-0111
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