The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
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Under argon protection conditions,300 mL of dried tetrahydrofuran (THF) was added to a 1 L three-necked flask,5-bromo-2-chloro-4-ethyldiphenylmethane (65.5 g, 200 mmol)The temperature of the reaction system was controlled at -78 C with an acetone /(N-BuLi) 80 mL (2.5 mol / L, 200 mmol, 1 eq) was slowly added dropwise. The temperature of the reaction system was controlled at -78 C or lower, and the reaction was continued at the end of the dropwise addition. hour;Then, 19.1 g (100 mmol) of cuprous iodide was slowly added to the reaction system, and the temperature of the reaction system was controlledIn the -40 ~ -30 reaction 1 hour, then slowly to the reaction system drip2,3,4,6-tetra-O-acetyl-alpha-D-pyran bromoglucoseTHF solution (41.5 g, 100 mmol, THF 100 mL, 0.5 eq) was added and the reaction temperature was controlled at -40 to -30 C during the addition and maintained at that temperature for 1 hour,After the addition was complete, the temperature of the reaction system was gradually returned to room temperature for 3 hours.After the reaction was quenched under ice cooling conditions with a saturated NaHCO3 solution to quench the reaction, extracted with ethyl acetate, and the combined organic phases, the organic phase with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a brown crude product was 59.8 g, 300 mL of anhydrous ethanol to give 53.1 g of a white solid (Compound 1:2-chloro-5- (2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl-1-yl)4′-ethoxydiphenylmethane),HPLC detection purity of 98.5% or more, the yield of 93%.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; Shenzhen Hanyu Pharmaceutical Co., Ltd.; Chen Xinliang; Yao Zhijun; Li Guotao; Liu Jian; Ma Yaping; Yuan Jiancheng; (13 pag.)CN104496952; (2017); B;,
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