4692-12-0Relevant articles and documents
Photoinitiated glycosylation at 350 nm
Cumpstey, Ian,Crich, David
experimental part, p. 469 - 485 (2012/06/15)
A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1→6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.
Glycosylation of triterpene alcohols and acids of the lupane and A-secolupane series
Klinotova, Eva,Krecek, Vaclav,Klinot, Jiri,Endova, Magdalena,Eisenreichova, Jana,Budesinsky, Milos,Sticha, Martin
, p. 1776 - 1798 (2007/10/03)
A series of 3- and 28-glucosides and glucosyl esters of betulinic acid (1a), 28-hydroxy-3,4-secolupa-4(23),20(29)-dien-3-oic acid (22a), dimethyl ester of 28-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid (43a), their 20(29)-dihydro derivatives (1b, 22b, 43b) and several other triterpenes of the lupane (12a, 12b) and 3,4-secolupane series (18a, 18b, 32a) has been prepared by reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide in acetonitrile in the presence of mercury(II) cyanide and subsequent deacetylation of the obtained tetra-O-acetyl-β-D-glucopyranosyl derivatives. In several cases attempted glucosylation in the presence of silver silicate afforded predominantly the corresponding 1,2-orthoacetates of α-D-glucopyranose.
An electrochemical synthesis of methyl α-isomaltoside
Hamann, Carl Heinz,Polligkeit, Herbert,Wolf, Peter,Smiatacz, Zygfryd
, p. 1 - 8 (2007/10/02)
A novel approach has been developed for the synthesis of methyl α-isomaltoside (10), comprising, as the first step, electrochemical conversion of the hydroxyl groups of methyl α-D-glucopyranoside into the corresponding anions.The anions subsequently react with tetra-O-acetyl-α-D-glucopyranosyl bromide to give methyl 2',3',4',6'-tetra-O-acetyl-α-isomaltoside (8) as the main product.O-deacetylation of which affords 10.The glycosidation proceeds under complete stereochemical control.Keywords: Isomaltoside, methyl α-; Disaccharides; Electrochemical synthesis; Structure