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Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95
Graphical Abstract
Figure 1: The tetrasaccharides associated with the pneumonicoccal serogroup 6.
Figure 2: Retrosynthetic analysis.
Scheme 1: Preparation of D-glucosyl donor 6. Reaction conditions: a) NapBr/PMBCl, NaH, DMF, rt, 12 h, 90% (6a...
Scheme 2: Preparation of L-rhamnosyl acceptor 5. Reaction conditions: a) Py, BzCl, rt, 12 h, 99%; b) DDQ, DCM...
Scheme 3: Preparation of ribitol acceptor 7. Reaction conditions: a) Me2C(OMe)2, pTSA, CH3COCH3, rt, 81%; b) ...
Scheme 4: Stepwise synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, DCM/Et2O (5:1), 4 Å MS, −3...
Scheme 5: One-pot synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, 4 Å MS, DCM/Et2O (4:1), N2,...
Beilstein J. Org. Chem. 2014, 10, 1488–1494, doi:10.3762/bjoc.10.153
Figure 1: Repeating unit of the A-band polysaccharide of P. aeruginosa.
Scheme 1: Preparation of the monomeric building blocks; reagents and conditions: i) Pyr., BzCl, 0 °C–rt; ii) ...
Scheme 2: Sequential stepwise synthesis of the trisaccharide; reagents and conditions: i) TMSOTf, DCM, molecu...
Scheme 3: Synthesis of the trisaccharide by sequential one-pot glycosylation reactions; reagents and conditio...
Scheme 4: Synthesis of the target trisaccharide via global deoxygenation strategy; reagents and conditions: i...