کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1390163 1500844 2015 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates
چکیده انگلیسی


• α-C-glycosyl-linked homoallylic tricloroacetimidates were prepared.
• Iodocyclization of these substrates gave highly substituted C-linked iodo-oxazines
• E- and Z-alkenes favored anti and syn 1,3-amino alcohol motifs, respectively.
• These products are potential precursors to C-glycosides of the glycolipid KRN7000.

The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.

The iodocyclization of homoallylic trichloroacetimidates provides precursors to C-linked glycolipids.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 407, 30 April 2015, Pages 148–153
نویسندگان
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