138528-01-5Relevant academic research and scientific papers
Synthesis of 1,2-anhydro-3,4,5-tri-O-benzyl-β-D-fructopyranose
Campbell, Malcolm M.,Heffernan, Gavin D.,Lewis, Terence
, p. 243 - 250 (1994)
A synthesis of the anomeric spiro-epoxide 15 from D-fructose, in 7 steps in an overall 13percent yield, is described.The key intermediate in the synthesis, 3,4,5-tri-O-benzyl-1-deoxy-1-iodo-β-D-fructopyranose (14), was prepared from the corresponding methyl fructopyranoside by reaction with the iodine-triphenylphosphine-imidazole reagent complex, followed by acid hydrolysis.Ring closure of the iodohydrin 14 was achieved under extremely mild conditions on treatment with silver(I) oxide in anhydrous THF.The 13C NMR spectrum of 15 exhibited a large upfield shift of the resonances assigned to C-1 and C-2, indicative of an oxirane ring involving these two carbon atoms.
Synthesis of α-Acyloxynitrones and Reactivity towards Samarium Diiodide
Racine, Emilie,Burchak, Olga N.,Py, Sandrine
, p. 4003 - 4012 (2016/08/24)
Upon treatment of fructose-derived nitrone 1 with samarium diiodide, with the aim of inducing its umpolung and coupling with electrophiles, an unexpected β-elimination of the benzyloxy group at C-1 was observed, yielding nitrone 2. The mechanism and scope
Synthesis of di- and trisaccharides comprising D-fructopyranose with β2→1 glycosidic linkage using β-D-fructopyranosyl fluoride as the fructosyl donor
Kaji, Eisuke,Kurimoto, Emiko,Saiga, Reiko,Matsuura, Ayako,Harada, Kazuho,Nishino, Takashi
, p. 453 - 468 (2007/10/03)
D-Fructose was converted into a stable, suitably protected fructosyl donor for iterative glycosylation, i.e., 1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride and a fructosyl acceptor, methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside in goo
Carbohydrate-derived spiroketals: Stereoselective synthesis of di-D-fructose dianhydrides
Benito, Juan M.,Rubio, Enrique,Gómez-García, Marta,Mellet, Carmen Ortiz,García Fernández, Jose M.
, p. 5899 - 5906 (2007/10/03)
A one-pot synthesis of di-D-fructose dianhydrides (DFAs) having the 1,6,9,13-tetraoxadispiro[4.2.4.2]tetradecane and 1,7,10,15-tetraoxadispiro[5.2. 5.2]hexadecane skeleton has been accomplished. The methodology relies on the ability of per-O-protected 1,2-O-isopropylidene β-D-fructofuranose and β-D-fructopyranose derivatives to undergo a tandem acetal cleavage-intermolecular glycosylation-intramolecular spiroketalization process by reaction with suitable acid promoters, such as boron trifluoride etherate or trifluoromethanesulfonic acid, in apolar organic solvents. Spirocyclization proceeds then under irreversible reaction conditions to give binary mixtures of di-D-fructofuranose (α,α and α,β diastereomers) or di-D-fructopyranose 1,2′:2,1′ dianhydrides (β,β and α,β), respectively, the stereochemical outcome being dependent on the non-participating or participating character of the protecting groups. Thus, benzylated and allylated derivatives afford, preferentially, the non-symmetric DFAs (α,β), with diastereomeric excess up to 92%. In contrast, the use of participating benzoyl groups favours the C2-symmetric diastereomer in both series.
