کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10606097 | 982946 | 2019 | 7 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Extension of the Nef reaction to C-glycosylnitromethanes
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Acid-catalysed methanolysis of 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-l-arabino-hex-1-enitol proceeds via a cascade set of consecutive reactions resulting in its regiospecific conversion to a mixture of α- and β-C-l-arabinofuranosylmethanal dimethyl acetals and a mixed internal methyl acetal. Structures of the final products of the overall process provide unique evidence that a kinetically controlled, five-membered-ring closure precedes a six-membered-ring closure in reversible systems capable of giving both five-membered and six-membered all-sp3-atom rings. Determination of the reaction intermediate enabled extension of the Nef reaction to C-glycosylnitromethanes. Protonated aci-nitro forms of C-glycosylnitromethanes that are resistant to the Nef reaction in aqueous acidic media undergo a modified Nef reaction in acidified methanol, and the corresponding C-glycosylmethanal dimethyl acetals with α-l-arabinopyranosyl, β-d-glucopyranosyl, β-d-galactopyranosyl, β-d-mannopyranosyl and β-l-rhamnopyranosyl configurations were obtained in moderate yields.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 341, Issue 12, 4 September 2006, Pages 2019-2025
Journal: Carbohydrate Research - Volume 341, Issue 12, 4 September 2006, Pages 2019-2025
نویسندگان
Mária PetruÅ¡ová, Michal Vojtech, Božena Pribulová, Erika Lattová, Mária Matulová, Monika Poláková, James N. BeMiller, VladimÃr KÅen, Ladislav PetruÅ¡,