کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1388582 1500904 2008 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-d-allofuranose: diastereoselective ether formation
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-d-allofuranose: diastereoselective ether formation
چکیده انگلیسی

Standard diazo transfer to 3-O-(2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-d-allofuranose (2), using p-acetamidobenzenesulfonyl azide (p-ABSA, 3) and DBU as base, provides the expected 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-d-allofuranose (4) as an orange syrup in 49% isolated yield. Subsequent decomposition of 4 using Rh2(OAc)4 yields ether 5 in a highly diastereoselective manner and in 58% isolated yield. The X-ray crystal structure of 5 proves that both newly produced stereocenters have the (S) configuration; the conformation of the ester group at O-3 of the furanose ring of 5 is used to discuss the possible cause of the observed stereoselectivity.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 343, Issues 10–11, 21 July 2008, Pages 1819–1823
نویسندگان
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