Glycosyl donors in “unusual” conformations – influence on reactivity and selectivity (original) (raw)

2011, Comptes Rendus Chimie

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Conformationally armed glycosyl donors: reactivity quantification, new donors and one pot reactions

Chemical Communications, 2008

General Information: 13 C-, 1 Hand H,H-COSY NMR were recorded on a Varian Mercury 400 (400MHz) NMR Instruments. The spectra were referenced to solvent residues. ES-MS was recorded on a Micromass LC-TOF instrument and MALDI-TOF MS was recorded on a Bruker Deltronics mass spectrometer using cinnamic acid (HCCA) based matrix. Optical rotations were measured on a PE-314 polarimeter at 20±1 °C. Chromatography was performed in Merck 60 silica. TLC was performed on Merck silica 60 E 254 coated glass plates and developed using Ce-mol (10 g Ce(IV)SO 4 and 15 g (NH 4) 2 MoO 4 in 1 L 10% H 2 SO 4 med) or phosphomolybic acid (MoO 3-H 3 PO 4 xH 2 O 5 % in EtOH) and subsequent heating. Figure S1. Glycosylation reactivities of different types of donors. Determining the relative rate of glycosylation: Each reaction was performed on 6 samples of 2 mL; each sample contained a solution of the appropriate donor in dichloromethane (different 0 0

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