Regio- and stereo-selective synthesis of carbohydrate isoxazolidines by 1,3-dipolar cycloaddition of nitrones to 5,6-dideoxy-1,2-O-isopropylidene- alpha-D-xylo-hex-5-enofuranose.
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.
al-Timari
U A
UA
Department of Organic Chemistry, Slovak Technical University, Bratislava, Czechoslovakia.
Fisera
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Goljer
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Ertl
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D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006027:Glycosides / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis*; D008353:Mannitol / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D006027:Glycosides; D006601:Hexoses; D007555:Isoxazoles; D009589:Nitrogen Oxides; C015388:nitrones; C057406:gulose; D008353:Mannitol; C076098:5,6-dideoxy-1,2-O-isopropylidenehex-5-enofuranose