کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1390455 | 983078 | 2011 | 9 صفحه PDF | دانلود رایگان |
O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides of d-gluco, d-galacto, and d-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-d-glycopyranosylamines with an axial C–N bond at the anomeric centre. In the presence of HgBr2, Hg(CN)2, or InCl3 the anomer of the above glycosylamine with an equatorial C–N bond was also isolated or detected. In CH3NO2 solutions as few as 5–10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-d-galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric α-amino acids.
Figure optionsDownload as PowerPoint slideHighlights
► Ritter-type reaction of C-(1-bromo-1-deoxy-D-glycopyranosyl)formamides.
► Synthesis of anomeric α-amino acid derivatives including peptides.
► Preparation of anomeric spiro-oxazoline derivatives.
Journal: Carbohydrate Research - Volume 346, Issue 14, 18 October 2011, Pages 2104–2112