Deoxy??nitrosugars. 6th communication. Stereoelectronic control in the reductive denitration of tertiary nitro ethers. A synthesis of 'C??glycosides'

F Baumberger, A Vasella

Index: Baumberger, Franz; Vasella, Andrea Helvetica Chimica Acta, 1983 , vol. 66, # 7 p. 2210 - 2222

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Citation Number: 105

Abstract

Abstract The separate, radical denitration with Bu 3 SnH of the pyranose derivatives 3, 4, 9, and 10 gave in good yields exclusively the 'C-glycosides'5 and 11, respectively (Scheme 1). Similar reduction of the cyclohexyl derivatives 15, 16, 19 and 20 gave 4: 1 mixtures of 17, 18, 21 and 22, respectively, always with predominant formation of an axial C, H-bond. In the furanose series a divergent behaviour was observed for the D-mannose-derived nitro ...