7115-19-7Relevant articles and documents
Regio- and stereochemical controlled koenigs-knorr-type monoglycosylation of secondary hydroxy groups in carbohydrates utilizing the high site recognition ability of organotin catalysts
Muramatsu, Wataru,Yoshimatsu, Hirofumi
supporting information, p. 2518 - 2524 (2013/10/21)
The catalytic regio- and stereoselective monoglycosylation of carbohydrates using organotin catalysts is demonstrated. The one-step reaction affords various oligosaccharides linked at the secondary hydroxy group in high chemical yield and good regio- and stereoselectivities. The regioselectivity of the glycosylation is shown to depend on the spatial arrangement of the hydroxy groups in the carbohydrates. Copyright
Intramolecular glycosidation by click reaction mediated spacer generation followed by spacer cleavage
Kumar, Amit,Geng, Yiqun,Schmidt, Richard R.
, p. 6846 - 6851 (2013/03/13)
2-O-Propargyl-substituted glycosyl donors and O-(2-azidobenzyl)-substituted acceptors having a vicinal hydroxy group readily underwent the click reaction. Intramolecular glycosidation with N-iodosuccinimide/trifluoromethansulfonic acid as the activating system afforded β-(1-3)- and α-(1-2)-linked disaccharides as part of 14-membered macrocycles. Descriptors for these reactions are proposed that consider the donor and acceptor attachment sites and the stereochemistry of the functional groups. Investigation of the influence of 2-O-linked 1-aryl-1,2,3-triazol-4-ylmethyl groups, as contained in the spacer, on the anomeric selectivity exhibited no anchimeric assistance. In addition, it was shown that the spacer group can be readily cleaved under Birch reduction conditions. The 1,2,3-triazole-forming click reaction was employed to generate glycosyl donor-spacer-acceptor constructs. Upon glycosidation, 14-membered macrocycles were obtained with high anomeric selectivity. Spacer cleavage was performed under Birch reduction conditions. Copyright
Enzymatic syntheses and selective hydrolysis of O-β-d- galactopyranosides using a marine mollusc β-galactosidase
Giordano, Assunta,Tramice, Annabella,Andreotti, Giuseppina,Mollo, Ernesto,Trincone, Antonio
, p. 139 - 143 (2007/10/03)
The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a β-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the
