Premium
Deoxy‐nitrosugars. 9th communication . Chain elongation of 1‐C ‐nitroglycosyl halides by substitution with some weakly basic carbanions
Author(s) -
Aebischer Bernrd,
Meuwly Roger,
Vesella Andrea
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670828
Subject(s) - chemistry , carbanion , nitromethane , halide , medicinal chemistry , lithium (medication) , enol , sulfide , walden inversion , bromide , dimethyl malonate , derivative (finance) , inorganic chemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , endocrinology , financial economics , economics
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 .