Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• reactivity of isosorbide and the non-toxic properties of DMC represent indeed a green match leading to several industrial appealing potential applications. Keywords: carbohydrate chemistry; D-sorbitol; dimethyl carbonate; green chemistry; isosorbide; Review Introduction In the last twenty years biorefinery

A robust synthesis of 7,8-didemethyl-8-hydroxy-5-deazariboflavin

• Matthias Bender,
• Henrik Mouritsen and
• Jens Christoffers

Beilstein J. Org. Chem. 2016, 12, 912–917, doi:10.3762/bjoc.12.89

• carbohydrate chemistry and might then allow purification and characterization of intermediate products. While we were following the synthetic approach by Yoneda et al. with a protected ribose derivative, Foss and co-workers were obviously facing the same preparative problem. To our surprise and delight (that

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

• Madhuri Vangala and
• Ganesh P. Shinde

Beilstein J. Org. Chem. 2015, 11, 2289–2296, doi:10.3762/bjoc.11.249

• carbohydrate chemistry, they are versatile intermediates in the synthesis of N-linked glycoproteins [20][21][22]. In the context of carbohydrate chemistry, there are two possible regioisomers for glycooxazolines. Firstly, the C1 O-linked 1,2-glycooxazolines (Figure 1, 5) are formed by intramolecular

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

• successfully prepared [19]. The Suzuki cross-coupling is particularly suitable for carbohydrate chemistry due to the mild reaction conditions and its tolerance to a variety of functional groups [20]. In addition, the reactions are easy to perform and the required boronic acids exhibit exceptional stabilities

Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

• Alafia A. Ansari,
• Y. Suman Reddy and
• Yashwant D. Vankar

Beilstein J. Org. Chem. 2014, 10, 300–306, doi:10.3762/bjoc.10.27

• , which has been well-explored for a variety of reactions in literature [37][38]. CAN was utilized successfully in carbohydrate chemistry for important transformations such as the azidonitration of glycals and the formation of 2-C-branched glycosides from glycals [39][40][41]. In this paper, we report on

Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• Zijie Li Yahui Gao Hideki Nakanishi Xiaodong Gao Li Cai The Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, 214122, China School of Food Science and Technology, Jiangnan University, Wuxi, 214122, China Division

Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed–disarmed strategy

• Abhijeet K. Kayastha and
• Srinivas Hotha

Beilstein J. Org. Chem. 2013, 9, 2147–2155, doi:10.3762/bjoc.9.252

• carbohydrate chemistry was first reported for the oxidation of alcohols [11][12][13][14][15][16]. However, until recently these catalysts were scarcely applied. Glycosidation is one of the key reactions in chemistry of carbohydrates, in which a nucleophile attaches to a saccharide to form a glycoside. In this

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

• hydrogenolysis is widely used in carbohydrate chemistry as a means to achieve the final deprotection step, few examples for hydrogenolytic cleavage of an oligosaccharide from a support have been reported [39][40]. To assemble oligosaccharides, linker 1 was equipped with a primary hydroxy group as a glycosylation

Synthesis in the glycosciences II

• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2012, 8, 411–412, doi:10.3762/bjoc.8.45

• contributions from renowned research groups in carbohydrate chemistry [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. This series impressively demonstrated the power and the passion, the creativity and the cleverness of modern synthetic glycoscience. But this success is on a continuing journey. Thus

• us go. It is interesting to see that, following this editorial approach, the diversity of titles reflects the diversity of carbohydrate chemistry and biology. There is no other class of natural products with a comparable potential for molecular diversity. There are no other biopolymers so difficult

One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation–decarbonylative alkynylation–cyclocondensation sequences

• Charlotte F. Gers,
• Julia Rosellen,
• Eugen Merkul and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1173–1181, doi:10.3762/bjoc.7.136

• in a wide range of cosmetic formulations [30]. In addition, numerous azulene derivatives display appealing properties for material [31][32][33] and pharmaceutical sciences [34][35][36][37][38]. Furthermore, the use of the azulene moiety as part of a protecting group chromophore in carbohydrate

• chemistry has recently been reported [39]. N-Heteroaryl-substituted azulenes can be accessed by stoichiometric [40][41] as well as Pd-catalyzed cross-coupling processes [42][43][44]. However, these methods have only delivered a narrow range of derivatives. Prior to application in Pd-catalyzed processes

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• , carbamate and thiourea-linked sugars The replacement of amide groups by pseudoamide (NH–C = X)–Y; X, Y = O, N, S) has been widely used in peptide chemistry to induce well-defined secondary structures. In carbohydrate chemistry, the incorporation of pseudoamide-type intersaccharide linkages has an additional

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

• much fervent study in the last two decades, and has led to many significant developments [10][11]. However, despite these advances, modern synthetic carbohydrate chemistry has still to provide a general method for the efficient synthesis of 1,2-cis-α-glycosidic linkages. In 2005 Boons and co-workers

Synthesis in the glycosciences

• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2010, 6, No. 16, doi:10.3762/bjoc.6.16

• presented in this series. Furthermore, carbohydrate chemistry is presented in the context of chemical biology together with organic chemistry making use of known chemical reactions as well as the stereochemical advantages of saccharides to construct novel molecules with unique properties. It has been a joy

Looking forward to volume six

• Jonathan Clayden

Beilstein J. Org. Chem. 2010, 6, No. 1, doi:10.3762/bjoc.6.1

• way within the journal, these papers can be viewed together using the “thematic series” tool on the website. Recent series have covered the topical themes of flow chemistry [1], supramolecular chemistry [2] and liquid crystals [3], and further series on carbohydrate chemistry and on organofluorine

Acid- mediated reactions under microfluidic conditions: A new strategy for practical synthesis of biofunctional natural products

• Katsunori Tanaka and
• Koichi Fukase

Beilstein J. Org. Chem. 2009, 5, No. 40, doi:10.3762/bjoc.5.40

• b for our N-glycan synthesis. Reductive opening of sugar 4,6-O-benzylidene acetals by the combination of acid/hydride reagents is one of the most useful transformations in the field of carbohydrate chemistry [49], not only for our current N-glycan case, since the benzyl-protected derivatives at

Convenient method for preparing benzyl ethers and esters using 2-benzyloxypyridine

• Susana S. Lopez and
• Gregory B. Dudley

Beilstein J. Org. Chem. 2008, 4, No. 44, doi:10.3762/bjoc.4.44

• suitable for the synthesis of halobenzyl ethers [25], which are emerging from their niche in natural products synthesis [26] because of their growing importance in carbohydrate chemistry [27][28][29][30][31]. The experiment outlined in Scheme 4 suggests that the observations described in this article for