کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1388991 982834 2009 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of regioselectively sulfated xylodextrins and crystal structure of sodium methyl β-d-xylopyranoside 4-O-sulfate hemihydrate
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis of regioselectively sulfated xylodextrins and crystal structure of sodium methyl β-d-xylopyranoside 4-O-sulfate hemihydrate
چکیده انگلیسی

Methyl xylobioside and methyl xylotrioside were prepared from the peracetylated anomeric xylosyl trichloroacetimidates by reaction with methanol followed by Zemplén deacetylation. Methyl β-d-xylopyranoside, methyl β-d-xylobioside and methyl β-d-xylotrioside were subjected to treatment with dibutyltin oxide followed by reaction with the trimethylamine/sulfur trioxide complex in tetrahydrofuran. This way, preferential sulfation of the terminal 4-hydroxy group at the nonreducing xylopyranosyl unit was achieved. In addition, partial sulfation at position 2 of the distal xylose unit was observed. The substitution pattern was derived from NMR spectroscopic data and was confirmed by the X-ray structure determination of sodium methyl β-d-xylopyranoside 4-O-sulfate. The compound crystallized as a hemihydrate in a triclinic lattice of space group P1 and possesses a pseudomonoclinic 2D supramolecular structure. The sulfation of free pentose oligomers via their intermediate stannylene acetals may thus be exploited to generate biologically active oligosaccharides for biomedical applications.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 344, Issue 1, 5 January 2009, Pages 21–28
نویسندگان
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