Carbohydrate research

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

UAR Al-Timari, Ľ Fišera

Index: Al-Timari, Usama A. R.; Fisera, Lubor Carbohydrate Research, 1991 , vol. 218, # 1 p. 121 - 127

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Citation Number: 16

Abstract

Abstract The synthesis of 3-aryl-5-(1, 2-O-isopropylidene-α-d-xylo-tetrofuranos-4-yl)-2- isoxazoline (3) from arylnitrile oxides and 5, 6-dideoxy-1, 2-O-isopropylidene-α-d-xylo-hex-5- enofuranose (1) is described. The 1, 3-dipolar cycloaddition reactions give mainly anti- adducts (⩾ 95% π-facial stereoselectivity).