3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry

被引：40

作者：

Andersen, Sofie Meng ^{[1
]}

Heuckendorff, Mads ^{[1
]}

Jensen, Henrik H. ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

关键词：

GLYCOSYL DONORS; O-GLYCOSYL; PRINCIPLES; THIOLS;

D O I：

10.1021/acs.orglett.5b00041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：944 / 947

页数：4

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