کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10605619 | 982784 | 2011 | 8 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
![عکس صفحه اول مقاله: Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation](/preview/png/10605619.png)
چکیده انگلیسی
Glycosylation studies for the construction of 1,2-cis α-linkages with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including d-mannosyl and l-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH2Cl2, Et2O, and acetonitrile as solvents. A non-participating solvent such as CH2Cl2 at â78 °C, favored the α-d-configuration. In contrast, acetonitrile strongly favored the β-d-configuration, whereas no selectivities were observed with Et2O. The use of thiophene as an additive did not enhance the α-d-selectivity as in the pyranose counterpart. Although selectivities strongly depended on the acceptor, trichloroacetimidate 1 constitutes a valuable donor for the synthesis of α-d-Galf-(1â2)-l-Rha and α-d-Galf-(1â6)-d-Man. As these motifs are present in pathogenic microorganisms, these procedures described here are useful for the straightforward synthesis of natural oligosaccharides.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 346, Issue 12, 6 September 2011, Pages 1495-1502
Journal: Carbohydrate Research - Volume 346, Issue 12, 6 September 2011, Pages 1495-1502
نویسندگان
Gabriel Gola, Mariano J. Tilve, Carola Gallo-Rodriguez,