Deoxy‐nitrosugars. 9th communication. Chain elongation of 1‐C ‐nitroglycosyl halides by substitution with some weakly basic carbanions

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