Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing
Abstract: A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity—a prerequisite for the flow experiments—no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.
Aronow, Jonas,Stanetty, Christian,Baxendale, Ian R.,Mihovilovic, Marko D.
p. 11 - 19
(2018/11/27)
Facile synthesis of methyl α- and β-d-[6-3H]galactofuranosides from d-galacturonic acid. Substrates for the detection of galactofuranosidases
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.
Bordoni, Andrea,Lima, Carlos,Marino, Karina,de Lederkremer, Rosa M.,Marino, Carla
p. 1863 - 1869
(2008/12/22)
High-yielding one-step conversion of D-glucose and D-galactose to the corresponding α and β methyl-D-glucofuranosides and galactofuranosides
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.
Lubineau,Fischer
p. 815 - 818
(2007/10/02)
A NEW, FACILE METHOD FOR CLEAVAGE OF ACETALS AND DITHIOACETALS IN CARBOHYDRATE DERIVATIVES
Treatment of carbohydrate acetals and dithioacetals with a dilute solution of iodine in methanol provides a simple, convenient, and high-yielding process for cleavage of the acetal functions.
Szarek, Walter A.,Zamojski, Aleksander,Tiwari, Kamal N.,Ison, Edward R.
p. 3827 - 3830
(2007/10/02)
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