3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry
3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry
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DOI：
10.1021/acs.orglett.5b00041
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发表时间：
2015-02-20
期刊：
影响因子：
5.2
通讯作者：
Jensen, Henrik H.
中科院分区：
文献类型：
--
作者：
Andersen, Sofie Meng;Heuckendorff, Mads;Jensen, Henrik H.
发现廉价的3-（二甲氨基）-1-丙胺（DMAPA）在异头脱酰反应中是有效的，以高产率得到1-O脱保护糖作为用于形成亚氨酸酯糖基供体的前体。还发现DMAPA可用于除去过量的试剂，例如苯甲酰氯、甲苯磺酰氯和2，2，2-三氟-N-苯基亚氨酰氯。脱酰反应可以在潮湿的THF中进行，并且不需要色谱纯化，因为酸性洗涤足以除去过量的试剂和形成的副产物。
Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.