The McKenna reaction – avoiding side reactions in phosphonate deprotection

• Katarzyna Justyna,
• Joanna Małolepsza,
• Damian Kusy,
• Waldemar Maniukiewicz and
• Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

• ), and therefore its easy removal from the reaction mixture. Section 4: Exchange of chloride for bromide BTMS is known to act as brominating agent for various functional groups, such as alcohols [47][48], three- and four-membered cyclic ethers [49], and anomeric glycosyl acetates [50]. However, to the

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• ]. Some of them have been obtained by coupling protected glycosyl thiolates and n-alkyl halides [14][15][16]. Moreover, mechanochemical thioglycosylation of glycosyl acetates was used for the synthesis of n-alkyl 1-thio-α--glycosides as carbohydrate mesogens [17]. Unfortunately, the preparation of alkyl

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

• A. Michael Downey and
• Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

• -pot method to obtain glycosyl acetates in the absence of protecting groups [84]. They determined that the order of addition of the reagents was important. First DMC, thioacetic acid and the base are mixed and then the saccharide is added last. Again DMC was utilized as the anomeric activating agent

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

• Tamashree Ghosh,
• Abhishek Santra and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 974–982, doi:10.3762/bjoc.9.112

• enzymatic hydrolysis, several thioglycosides have been evaluated as enzyme inhibitors [13][14]. As a consequence a large number of reports have appeared in the past for the preparation of thioglycosides. Conventionally, thioglycosides are prepared by the reaction of glycosyl acetates with thiols or

• ]; and (c) conversion of glycosyl acetates and bromides to isothiouronium salts followed by hydrolytic alkylation of isothiouronium salts with alkyl halide in the presence of a base [26][27]. Most of the reactions have several shortcomings, which include formation of an anomeric mixture of the products

Benzyne arylation of oxathiane glycosyl donors

• Martin A. Fascione and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2010, 6, No. 19, doi:10.3762/bjoc.6.19

• sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols. Keywords: benzyne; 1,2-cis-glycosides; glycosyl acetates; oxathiane glycosyl donors