کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1348007 980334 2008 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Isomerization as a route to rare ketoses: the beneficial effect of microwave irradiation on Mo(VI)-catalyzed stereospecific rearrangement
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Isomerization as a route to rare ketoses: the beneficial effect of microwave irradiation on Mo(VI)-catalyzed stereospecific rearrangement
چکیده انگلیسی

Mo(VI)-catalyzed isomerization of easily accessible 2-C-(hydroxymethyl)-branched aldoses to rare ketoses was achieved in 3 min using microwave flash heating. This contribution highlights the remarkable advantages of Mo(VI) catalysis and the beneficial effects of microwave irradiation in carbohydrate synthesis. The transformation yielded the respective ketoses in good yields (46–86%). Furthermore, the potential of the Mo(VI)-catalyzed transformation was studied using a new branched 6-deoxy-aldose to prepare 7-deoxy-l-gluco-heptulose. The method is fast and useful for the preparation of rare ketoses under microwave conditions.

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6-Deoxy-2,3-O-isopropylidene-l-manno-pyranoseC9H16O5Ee = 100%[α]D = −11.0 (c 1.0, acetone)Source of chirality: 6-deoxy-l-mannose (l-rhamnose)Absolute configuration: (2S,3S,4S,5S)

6-Deoxy-2,3-O-isopropylidene-2-C-(hydroxymethyl)-l-manno-pyranoseC10H18O6Ee = 100%[α]D = −18.0 (c 1.0, acetone)Source of chirality: 6-deoxy-l-mannose (l-rhamnose)Absolute configuration: (2S,3S,4S,5S)

6-Deoxy-2-C-(hydroxymethyl)-l-mannoseC7H14O6Ee = 100%[α]D = −12.0 (c 1.0, H2O)Source of chirality: 6-deoxy-l-mannose (l-rhamnose)Absolute configuration: (2S,3S,4R,5S)

7-Deoxy-l-gluco-heptuloseC7H14O6Ee = 100%[α]D = −40.0 to −38.0 (c 1, H2O)Source of chirality: 6-deoxy-l-mannose (l-rhamnose)Absolute configuration: (1R,2R,3S,4R,5S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 2, 6 February 2008, Pages 204–208
نویسندگان
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