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Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxyglycosides from 3-O-Acetyl-2-nitroglycals
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2022-06-20 , DOI: 10.1002/ejoc.202200519
Xiaopei Wu 1 , Zhichao Zheng 1 , Liming Wang 1 , Yunxia Xue 1 , Jinxi Liao 1 , Hui Liu 1 , Deyong Liu 1 , Jian-Song Sun 1 , Qingju Zhang 2
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A novel method for 2-nitroglycals synthesis was developed. Using 3-O-acetyl-2-nitroglycal as donors, we investigated the efficient method for 2,3-diamino-2,3-dideoxy-glycosides synthesis via organobase 4-pyrrolidinopyridine (PPY) mediated relay glycosylation. The method has many advantages including mild reaction condition, excellent site-selectivity and stereoselectivity, good to excellent yield, broad substrate scopes and one-pot procedure.

中文翻译:

从 3-O-乙酰基-2-硝基甘醇立体选择性合成 2,3-二氨基-2,3-双脱氧糖苷

2-Nitroglycal 是一种广泛用于氨基糖苷类合成的合成子。在此,我们报告了一种使用 n Bu 4 NNO 3 /Tf 2 O/DTBMP 合成 2-硝化糖的有效方法。使用 3-O-acetyl-2-nitroglycals 作为供体,使用 4-pyrrolidinopyridine (PPY) 介导的中继建立了一种构建具有挑战性的 1,2-cis-2,3-diamino-2,3-dideoxyglycosidic 键的新方法糖基化反应。该方法具有许多特点,包括非常温和的反应条件、优异的区域和立体选择性、良好的收率和广泛的底物范围。
更新日期:2022-06-20
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