Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

•  4). The reaction between Nam (1a) and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (2a) in acetonitrile at room temperature resulted in the corresponding triacetate derivative of NR+ triflate (OTf−) 9a which was converted without isolation into NR+OTf− by methanolysis. The final N-glycoside contained 13

AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

• Jayashree Rajput,
• Srinivas Hotha and
• Madhuri Vangala

Beilstein J. Org. Chem. 2018, 14, 682–687, doi:10.3762/bjoc.14.56

• -benzoylated disaccharides needed 2–3 h of heating at 55 °C. Keywords: acylated sugars; azidation; gold(III) bromide; N-glycoside; oxophilicity; Introduction The past few decades had seen the enrichment of transition metal complexes in various glycosylation strategies [1]. In particular, gold complexes with

Acylsulfonamide safety-catch linker: promise and limitations for solid–phase oligosaccharide synthesis

• Jian Yin,
• Steffen Eller,
• Mayeul Collot and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 2067–2071, doi:10.3762/bjoc.8.232

• activated by TMSOTf were conducted, and followed by Zemplén cleavage. Similarly, three equivalents of thioglycosides 17 and 19 were added three times (triple coupling) for each glycosylation employing DMTST or NIS/TfOH as an activator. In both instances, surprisingly, only N-glycoside 20 (minor product) and

• -phase oligosaccharide synthesis were discovered. The sulfamyl group can be attacked by excess glycosylating agent to give the unexpected resin-bound N-glycoside, which may block additional reaction sequences and extension of the oligosaccharide [28]. In addition, sodium methoxide can directly cleave the

Synthesis and structure of tricarbonyl(η⁶-arene)chromium complexes of phenyl and benzyl D-glycopyranosides

• Thomas Ziegler and
• Ulrich Heber

Beilstein J. Org. Chem. 2012, 8, 1059–1070, doi:10.3762/bjoc.8.118

• reacting acetobromoglucose with 6-tert-butyl-2-hydroxypyridine [20] under Helferich conditions (Hg(CN)2). Only the corresponding O-glycoside 1l was obtained, and no N-glycoside was formed in this Helferich glycosylation (Scheme 1). Sterically hindered 6-tert-butyl-2-hydroxypyridine was chosen as the