ChemInform Abstract: Stereoselective Synthesis of C-Glycosylphosphonates from Their Ketols. Reconsideration of an Abandoned Route

Autor:	Claudia Pasti, Alberto Marra, Alessandro Dondoni
Rok vydání:	2010
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Pyranose Chemistry Stereochemistry Glycosyl Stereoselectivity General Medicine Furanose Phosphonate
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
Popis:	Isosteric phosphonate analogues of glycosyl 1-phosphates have been obtained by addition of LiCH 2 P(O)(OMe) 2 to glyconolactones followed by Et 3 SiH–TMSOTf reductive dehydroxylation of the resultant ketols. The compounds prepared include four β-linked pyranose derivatives ( d - galacto , 2-azido-2-deoxy- d - galacto , d - gluco , d - manno ) and one β-linked furanose derivative ( d - manno ). In the latter case the ketol was activated as its 2-acetate. In agreement with an observation in another laboratory, the dehydroxylation of a model ketol phosphonate failed with the use of Et 3 SiH–BF 3 ·Et 2 O.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::25ec723aadd07b8546772fb214d7e288 https://doi.org/10.1002/chin.200025207 Zobrazit plný text záznamu Plný text