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Reactions with and in Anhydrous Hydrogen Fluoride, 13. A Convenient One-Pot Synthesis of Glucofurano<2,1-d>oxazolines with an Additional 3,5,6-Orthoester Function
The reactions of dioxolanylium and oxazolinium ions, formed in anhydrous HF from N-acylated 2-amino-2-deoxy-D-glucoses and one equivalent of carboxylic acid anhydride or chloride, were investigated by treatment of their HF solutions with triethylamine/alkane or triethylamine/ether systems.Thus, the 2-acylamido-2-deoxy-D-glucoses 1 and 2 react with acetic anhydride, dodecanoic anhydride or pivaloyl chloride in anhydrous HF at -30 deg C to give 5,6-dioxolanylium ions.On treatment with formic acid at room temperature they undergo further reaction to yield the thermodynamically favored 3,6-anhydro derivatives.The glucofurano-oxazolines 3-5, containing an orthoester substructure, as well as the 3,6-anhydro-D-glucofuranose derivatives 6 and 7 can be isolated after treatment of the HF solutions with triethylamine.The oxazoline derivative 4 was used as glycosyl donor for methanol giving the methyl glycoside 8 without cleavage of the orthoester moiety. – Key Words: Hydrogen fluoride, anhydrous / Glucosamines / Orthoesters / Oxazolines / Glycosylation / Carbohydrates
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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics