Reaction of Enohexopyranoside Acetates with Lithium Dimethylcuprate(I) and Its Application to Synthesis of Prelog-Djerassi Lactone

Autor:	Hironobu Hashimoto, Nobuya Kawauchi
Rok vydání:	1987
Předmět:	chemistry.chemical_classification Chemistry Substitution (logic) chemistry.chemical_element Glycoside Organic chemistry SN2 reaction Lithium General Chemistry Nuclear magnetic resonance spectroscopy Methylation Lactone
Zdroj:	Bulletin of the Chemical Society of Japan. 60:1441-1447
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.60.1441
Popis:	In the reaction of two 2-O-acetyl-3-enohexopyranosides and four 4-O-acetyl-2-enohexopyranosides including 2-C-methyl and 4-C-methyl derivatives, respectively, with lithium dimethylcuprate(I), anti SN2′ substitution was proved to be preferential, giving the corresponding C-methylated derivatives. On the other hand, SN2 substitution occurred in the reaction of the 2-enopyranoside without methyl branch and D-glucal triacetate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0a59f8b82b5938f4d39f783549c324ea https://doi.org/10.1246/bcsj.60.1441 Zobrazit plný text záznamu