[关键词]
[摘要]
目的 设计并合成1-[3-(3-苄基-4-乙氧基苄基)-4-氯苯基]-1,6-二脱氧-β-D-吡喃葡萄糖。方法 以5-溴-2-氯-4'-乙氧基二苯甲烷为原料,通过Friedel-Crafts酰基化、还原、亲核加成、还原乙酰化、脱乙酰化反应的得到目标化合物。结果 根据理化性质和波谱数据鉴定了目标化合物的结构,总收率为32%,质量分数为98.48%。结论 1-[3-(3-苄基-4-乙氧基苄基)-4-氯苯基]-1,6-二脱氧-β-D-吡喃葡萄糖的合成为tianagliflozin中杂质的研究提供了方便。
[Key word]
[Abstract]
Objective To design and synthesize 1-[3-(3-benzyl-4-ethoxybenzyl)-4-chlorophenyl]-1,6-dideoxy-β-D-glucopyranose. Methods 5-Bromo-2-chloro-4'-ethoxydiphenylmethane was used as starting material to synthesize the target compound by Friedel - Crafts acylation, reduction, nucleophilic addition, reduction acetylation, and deacetylation reactions. Results The structure of target compound was identified on the basis of physicochemical properties and spectroscopic data. The overall yield of the synthetic route was 32% and the purity was 98.48%. Conclusion The synthesis of 1-[3-(3-benzyl-4-ethoxybenzyl)-4-chlorophenyl]-1,6-dideoxy-β-D-glucopyranoside provides the convenience for the study of impurities in tianagliflozin.
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[基金项目]
国家自然科学基金资助项目(21302141);天津市科技计划项目(10ZCKFSH01300);天津市应用基础与前沿技术研究计划项目(14JCQNJC12900)