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

Autor:	Andrea Vesella, Roger Meuwly, Bernrd Aebischer
Rok vydání:	1984
Předmět:	Nitromethane Stereochemistry Organic Chemistry Halide Biochemistry Enol Chloride Medicinal chemistry Catalysis Sodium sulfide Diethyl malonate Inorganic Chemistry chemistry.chemical_compound chemistry Bromide Drug Discovery medicine Physical and Theoretical Chemistry medicine.drug Carbanion
Zdroj:	Helvetica Chimica Acta. 67:2236-2241
ISSN:	1522-2675 0018-019X
DOI:	10.1002/hlca.19840670828
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bb2e39611814ab2d61e3811552901e06 https://doi.org/10.1002/hlca.19840670828 Zobrazit plný text záznamu Plný text