Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives

Autor:	Hiroshi Fukase, Satoshi Horii
Rok vydání:	1992
Předmět:	Aminocyclitol chemistry.chemical_classification chemistry.chemical_compound chemistry Aldose Stereochemistry Valienamine Organic Chemistry Aldonic acid Moiety Epimer Protecting group Reductive amination
Zdroj:	The Journal of Organic Chemistry. 57:3651-3658
ISSN:	1520-6904 0022-3263
Popis:	Novel synthetic routes to valiolamine (1a) and N-substituted valiolamine derivatives via branched-chain inosose derivatives are described. (1S)-(1(OH),2,4/1,3)-2,3,4-tri-O-benzyl-1-C- [(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (3), a branched-chain inosose derivative prepared from D-glucose,has been converted into 1a via a ketoxime followed by hydrogenation. N-Substituted valiolamine derivatives having strong α-D-glucosidase inhibitory activity have been synthesized by the direct reductive amination of the branched-chain inosose derivative 3 with an appropriate amino compound to construct the N-substituent moiety,followed by removal of the O-benzyl protecting group
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6219bb1c60a33f04406f2e56efa9c76b https://doi.org/10.1021/jo00039a026 Zobrazit plný text záznamu