Helvetica Chimica Acta p. 2210 - 2222 (1983)
Update date:2022-08-02
Topics:
Baumberger, Franz
Vasella, Andrea
The separate, radical denitration with Bu3SnH 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 cylohexyl 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 ethers 25 and 27 and the D-ribose-derived nitro ethers 30 and 31, respectively, in that the former two gave isomerically homogeneous reduction products (26 and 28, respectively; Scheme 3) and the latter a 1:1 mixture of the diastereoisomers 32 and 33 (Scheme 4).The stereochemical results were explained on the basis of the stereoelectronic effect of the ring O-atom, the preferred conformation of the intermediate, pyramidal alkoxyalkyl radicals and steric effects in the trioxabicyclo<3.3.0>octane ring system.
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