p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates

• Madhuri Vangala and
• Ganesh P Shinde

Beilstein J. Org. Chem. 2016, 12, 2086–2092, doi:10.3762/bjoc.12.197

• p-nitrophenyl carbonate of D-psicofuranose [28], n-pentenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside [32][33][34] and 2,3-di-O-benzyl-α-methyl-D-arabinofuranoside [35] (Table 2, 11a–13a) gave the γ-lactam-derived carbamates 11b–13b in 53%, 63% and 67% yield, respectively. As DBU and DBN are known to

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

• in toluene through nucleophilic addition of electron-rich nitriles to the oxacarbenium ion intermediate of 1,2;3,4-di-O-isopropylidene-β-D-psicofuranose derivatives with concomitant intramolecular trapping of the C2 hydroxymethyl group on the electrophilic nitrilium carbon. These carbohydrate-derived

• acetonitrile was shown, illustrating the instability of spirooxazolines in comparison with fused oxazolines [37]. In our work, the activation of the β-D-psicofuranose derivative 5a with TMSOTf in acetonitrile exclusively resulted in the formation of spirooxazoline 6a. The stability of this compound inspired us

• to explore the scope of the synthesis and isolation of spirooxazolines. Thus, the required key intermediate D-psicofuranose 2a was synthesized in four steps from the readily available starting material D-fructose following the literature procedure [42][47]. The C6–OH group of D-psicofuranose was

Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

• Maroš Bella,
• Miroslav Koóš and
• Chun-Hung Lin

Beilstein J. Org. Chem. 2015, 11, 1547–1552, doi:10.3762/bjoc.11.170

• strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by

• computational methods. After the attempted thioglycosylation of 11 with EtSH in the presence of BF3·OEt2, 2-methyloxazoline derivatives 13 and 14 were isolated. Keywords: glycosyltransferases; inhibitors; D-psicofuranose; synthesis; thioglycosylation; Introduction Glycosyltransferases (GTs) belong to a family

• charge distribution as it was calculated for the TS [9][10]. In this contribution, attention is focused on the synthesis of the saccharide moiety of potential GnTs inhibitors (framed structure in Figure 1). In this respect, a novel approach to 3-acetamido-3-deoxy-D-psicofuranose derivatives, based on the