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Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-iso-propylidene-α-d-xylo-hex-5-enofuranose

✍ Scribed by Usama A. R. Al-Timari; Ľubor Fišera

Publisher
Elsevier Science
Year
1991
Tongue
English
Weight
557 KB
Volume
218
Category
Article
ISSN
0008-6215

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✦ Synopsis

The synthesis of 3-aryl-5-( 1,2-O-isopropylidene-a-D-xylo-tetrofuranos-4-yl)-2-isox~oline (3) from arylnitrile oxides and 5,6-dideoxy-l,2-O-isopropylidene-a-D-xylo-hex-S-enofuranose (1) is described. The I ,3-dipolar cycloaddition reactions give mainly anti-adducts (3 95% n-facial stereoselectivity).

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✍ Usama A.R. Al-Timari; L̆ubor Fis̆era; Igor Goljer; Peter Ertl 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 540 KB

The synthesis of 2-phenyl-3-aryl and 2-phenyl-3-aroyl derivatives 5-(1,2-O-isopropylidene-alpha-D-xylo-tetrofuranos-4-yl)isoxazolidi ne (3) from nitrones and 5,6-dideoxy-1,2-O-isopropylidene-alpha-D-xylo-hex-5- enofuranose (1) is described. The 1,3-dipolar cycloaddition reactions given mainly anti a