1824-89-1Relevant academic research and scientific papers
Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides
Masui, Seiji,Manabe, Yoshiyuki,Hirao, Kohtaro,Shimoyama, Atsushi,Fukuyama, Takahide,Ryu, Ilhyong,Fukase, Koichi
supporting information, p. 397 - 400 (2019/02/26)
Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.
A Systematic Study of Metal Triflates in Catalytic Transformations of Glucose in Water and Methanol: Identifying the Interplay of Br?nsted and Lewis Acidity
Bodachivskyi, Iurii,Kuzhiumparambil, Unnikrishnan,Williams, D. Bradley G.
, (2019/04/25)
The specific type of acidity associated with the given metal trifloromethanesulfonates (Br?nsted or Lewis acidity) dramatically influences the course of reactions, and it is possible to select for disaccharides, fructose, methyl glucosides, or methyl levulinate. Glucose is transformed into a range of value-added molecules in water and methanol under the action of acidic metal triflates as catalysts, including their analogous Br?nsted acid-assisted or Br?nsted base-modified systems. A systematic study is presented of a range of metal triflates in methanol and water, pinning down the preferred conditions to select for each product.
Facile synthesis of methyl α- and β-d-[6-3H]galactofuranosides from d-galacturonic acid. Substrates for the detection of galactofuranosidases
Bordoni, Andrea,Lima, Carlos,Marino, Karina,de Lederkremer, Rosa M.,Marino, Carla
, p. 1863 - 1869 (2008/12/22)
Galactofuranose metabolism is a good target for the development of novel chemotherapeutic agents for the treatment of some microbial infections. A simple procedure for the synthesis of methyl (methyl α,β-d-galactopyranosid)uronate followed by NaB3H4 reduction gave a straightforward access to radiolabeled substrates for galactofuranosidases.
Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline
Cai, Ye,Ling, Chang-Chun,Bundle, David R.
, p. 4021 - 4024 (2007/10/03)
(Chemical Equation Presented) A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-D-glucopyranosides in good to high yields. Primary alcohols gave only β-D-glucopyranosides. A mechanism is proposed for this transformation.
Reaction of D-fructose, D-glucose and inulin with alcohols in the presence of iodine; a novel glycosidation procedure
Verhart, Cor G.J.,Fransen, Carel T.M.,Zwanenburg, Binne,Chittenden, Gordon J.F.
, p. 133 - 139 (2007/10/03)
An efficient procedure for the glycosidation of D-fructose and D-glucose catalyzed by iodine is described. The reaction yields mainly alkyl glycofuranosides. Treatment of inulin under similar conditions leads to inter-glycosidic bond cleavage and to formation of alkyl D-fructofuranosides. The reaction conditions are particularly mild and relatively selective.
High-yielding one-step conversion of D-glucose and D-galactose to the corresponding α and β methyl-D-glucofuranosides and galactofuranosides
Lubineau,Fischer
, p. 815 - 818 (2007/10/02)
D-Glucose and D-Galactose are transformed to the corresponding α and β-Methyl D-Glucofuranosides in good yields using methanol and Ferric chloride as catalyst.
