1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• -fused dihydrodithiin ring is first hydrodesulfurized and then dehydroxylated in a stereospecific and stereoselective manner [62]. The dihydrodithiin building block 66 thus acts as a synthetic equivalent of an allyl alcohol anion and serves as a versatile synthon for de novo carbohydrate synthesis [63

An efficient synthesis of 1,6-anhydro-N-acetylmuramic acid from N-acetylglucosamine

• Matthew B. Calvert,
• Christoph Mayer and
• Alexander Titz

Beilstein J. Org. Chem. 2017, 13, 2631–2636, doi:10.3762/bjoc.13.261

• cell wall recycling; carbohydrate synthesis; Introduction 1,6-Anhydro-N-acetylmuramic acid (AnhydroMurNAc, 1, Figure 1) and its derivatives (e.g., 2 and 3) are of great interest due to their integral role in bacterial cell wall recycling [1][2] and the induction of antibacterial resistance [3

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

• Raju Cheerlavancha,
• Ahmed Ahmed,
• Yun Cheuk Leung,
• Aggie Lawer,
• Qing-Quan Liu,
• Marina Cagnes,
• Hee-Chan Jang,
• Xiang-Guo Hu and
• Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

• Raju Cheerlavancha Ahmed Ahmed Yun Cheuk Leung Aggie Lawer Qing-Quan Liu Marina Cagnes Hee-Chan Jang Xiang-Guo Hu Luke Hunter School of Chemistry, The University of New South Wales, Sydney NSW 2052, Australia National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• needed [3]. However, this is hampered by the limited availability of complex glycans from nature. Thus, chemical synthesis is a powerful approach to provide much needed samples to enable biological studies [4]. Traditional carbohydrate synthesis is commonly carried out from the reducing end to the non

• acid synthesis. With continuous development, the preactivation strategy will achieve wider applications in complex carbohydrate synthesis. Representative structures of products formed by the preactivation-based dehydrative glycosylation of glycosyl hemiacetal. Retrosynthetic analysis of pentasaccharide

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

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

• Adesh Kumar Singh,
• Varsha Tiwari,
• Kunj Bihari Mishra,
• Surabhi Gupta and
• Jeyakumar Kandasamy

Beilstein J. Org. Chem. 2017, 13, 1139–1144, doi:10.3762/bjoc.13.113

• role in carbohydrate synthesis. Thioglycosides, glycosyl sulfoxides and sulfones have been widely used as glycosyl donors in oligosaccharide synthesis which can be activated under mild reaction conditions [5][6][7][8][9][10]. Glycosyl sulfoxide donors usually provide excellent anomeric selectivity

Indium-mediated allylation in carbohydrate synthesis: A short and efficient approach towards higher 2-acetamido-2-deoxy sugars

• Christopher Albler,
• Ralph Hollaus,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2014, 10, 2230–2234, doi:10.3762/bjoc.10.231

• Christopher Albler Ralph Hollaus Hanspeter Kahlig Walther Schmid Department of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna, Austria 10.3762/bjoc.10.231 Abstract Higher aminosugars are interesting targets in carbohydrate synthesis since these compounds play important

Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools

• Luciana Baldoni and
• Carla Marino

Beilstein J. Org. Chem. 2014, 10, 1651–1656, doi:10.3762/bjoc.10.172

• ; Introduction Anhydro sugars are formed by the intramolecular elimination of a water molecule, with the simultaneous formation of a new heterocyclic ring of different size. They are valuable intermediates not only in carbohydrate synthesis, but also as starting materials for other natural and non-natural

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• existing 3D structural information) together with links to corresponding entries in NCBI GenBank, UniProt [50] or PDB [40]. However, little information is provided about enzyme specificity, kinetics, or catalytic residues, which is crucial information if the enzymes are to be used in carbohydrate synthesis

Preparation of aminoethyl glycosides for glycoconjugation

• Robert Šardzík,
• Gavin T. Noble,
• Martin J. Weissenborn,
• Andrew Martin,
• Simon J. Webb and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2010, 6, 699–703, doi:10.3762/bjoc.6.81

• are not experienced in carbohydrate synthesis. Here we describe a systematic study with the aim of finding such robust and efficient methods for a number of commonly used mono- and disaccharides starting from commercially available reagents and with a minimal number of steps. In our studies no such