SummaryThe I-C-nitroglycosyl chloride 1 reacted with the anions from 2-nitropropane, nitromethane, and diethyl malonate, to give the chain-extended products 2 (81 %), 5 (72%), and 6 (83%0), respectively. Treatment of the 1-C-nitroglycosyl bromide 7 by the lithium salt obtained from 8 gave the dodecodiulose derivative 9 (76%). The /?+-configuration of 2 and 9 was inferred from their NMR and CD spectra. Treatment of 2 and 9 with sodium sulfide gave the enol ethers 3 (96 %) and 10 (92 %), respectively. The (2)-configuration of 10 was deduced from the configuration of its hydrogenation product 11.
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