Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

• Mayeul Collot,
• Steffen Eller,
• Markus Weishaupt and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 97–105, doi:10.3762/bjoc.9.13

• ], the need for synthetic tools has prompted synthetic carbohydrate chemists to develop methods for the accelerated synthesis of all types of glycans [9][10][11][12][13][14][15][16][17][18][19]. Automated synthesis of oligosaccharides is beginning to provide molecules for biological evaluation [20][21

Antifreeze glycopeptide diastereomers

• Lilly Nagel,
• Carsten Budke,
• Axel Dreyer,
• Thomas Koop and
• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1657–1667, doi:10.3762/bjoc.8.190

• ) for the retro-inverso peptides. All cycles for the synthesis of the glycosylated peptides and aglycons follow a published procedure [16][23]. The automated synthesis of the aglycons was performed under microwave irradiation at a maximum of 78 °C at 35 W, whereas for the glycopeptides lower

Automated synthesis of sialylated oligosaccharides

• Davide Esposito,
• Mattan Hurevich,
• Bastien Castagner,
• Cheng-Chung Wang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

• sialyl α-(2→3) and α-(2→6) galactosyl imidates, which, used in combination with the automated platform, provided rapid access to a small library of conjugation-ready sialosides of biological relevance. Keywords: automated synthesis; disaccharide building blocks; solid-phase synthesis; sialic acid

• this important class of molecules. The automated synthesis of oligosaccharides has been significantly improved since the first report in 2001 [4]. Currently, the platform enables the rapid assembly of complex oligosaccharides and accommodates the most commonly employed glycosylation reactions [5][6][7

• automated synthesis requires readily accessible building blocks that can be used in excess to drive reactions to completion. As our initial goal, we developed a method to provide sialic acid containing disaccharide glycosylating agents with minimal synthetic effort. Simple N-acetyl building blocks such as 1

Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

• Kalicharan Chattopadhyay,
• Erik Fenster,
• Alexander J. Grenning and
• Jon A. Tunge

Beilstein J. Org. Chem. 2012, 8, 1200–1207, doi:10.3762/bjoc.8.133

• nucleophiles by using palladium(0) as a catalyst (Scheme 1). In addition, given the known biological activity of aminomethylcoumarins, we prepared a 128-member library of aminated coumarins using rapid automated synthesis. Results and Discussion To begin investigating the diversification of

• molecules (Figure 2). To begin, an 8 × 16 library (coumarin C1–8 × amine A1–16) of aminomethylcoumarins was devised for preparation by using a Chemspeed SLT100 automated synthesizer. For automated synthesis, the procedure and workflow was modified somewhat for optimal yield. Specifically, the loading of Pd

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S_NAr reaction

• Charlotte Wiles and
• Paul Watts

Beilstein J. Org. Chem. 2011, 7, 1360–1371, doi:10.3762/bjoc.7.160

• ® S1) was employed for the continuous flow synthesis of diaryl ethers at 195 °C and 25 bar, affording a reduction in reaction time from tens of minutes to 60 s when compared with a stopped-flow microwave reactor. Keywords: automated synthesis; continuous flow; microreactor; microwave; nucleophilic