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Regio- and stereo-selective synthesis of carbohydrate isoxazolidines by 1,3-dipolar cycloaddition of nitrones to 5,6-di-deoxy-1,2-O-isopropylidene-α-d-xylo-hex-5-enofuranose

✍ Scribed by Usama A.R. Al-Timari; L̆ubor Fis̆era; Igor Goljer; Peter Ertl

Publisher
Elsevier Science
Year
1992
Tongue
English
Weight
540 KB
Volume
226
Category
Article
ISSN
0008-6215

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✦ Synopsis

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 adducts 3 and 4 (greater than or equal to 95% pi-facial stereoselectivity). The cycloadducts 3 with H-3,5 cis are formed either exclusively or preponderate over the trans diastereoisomers 4.

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Regioselective synthesis of C-nucleoside
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
✍ Usama A. R. Al-Timari; Ľubor Fišera 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 557 KB

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)