کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1349188 980387 2010 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Microwave-assisted regioselective synthesis and isomerization of 6-O-vanillyl- and 6-O-iso-vanillyl hexoses and studies of their activities as radical scavengers by EPR spectroscopy
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Microwave-assisted regioselective synthesis and isomerization of 6-O-vanillyl- and 6-O-iso-vanillyl hexoses and studies of their activities as radical scavengers by EPR spectroscopy
چکیده انگلیسی

Four 6-O-substituted saccharides, namely 6-O-vanillyl-d-glucose 1, 6-O-vanillyl-d-mannose 2, 6-O-iso-vanillyl-d-glucose 3 and 6-O-iso-vanillyl-d-mannose 4 have been synthesized. Synthesized saccharide derivatives have been subsequently used in Mo(VI)-catalyzed stereospecific isomerizations yielding compounds with potential radical scavenging activity. In order to accelerate intramolecular isomerization rates and conversions microwave irradiation was used. Synthesized products were obtained with excellent stereoselectivity in good conversions and were tested by EPR spectroscopy for radical scavenging activity.

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6-O-(4-Hydroxy-3-methoxybenzyl)-d-glucoseC14H20O8Ee = 100%[α]D=+33.0[α]D=+33.0 (c 1.0, MeOH)Source of chirality: d-glucose

6-O-(4-Hydroxy-3-methoxybenzyl)-d-mannoseC14H20O8Ee = 100%[α]D=+15.0[α]D=+15.0 (c 1.0, MeOH)Source of chirality: d-mannose

6-O-(3-Hydroxy-4-methoxybenzyl)-d-glucoseC14H20O8Ee = 100%[α]D=+31.0[α]D=+31.0 (c 1.0, MeOH)Source of chirality: d-glucose

6-O-(3-Hydroxy-4-methoxybenzyl)-d-mannoseC14H20O8Ee = 100%[α]D=+13.0[α]D=+13.0 (c 1.0, MeOH)Source of chirality: d-mannose

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 21, Issue 6, 8 April 2010, Pages 756–761
نویسندگان
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