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Typical Experimental Procedure: To a solution of thioglycoside (1.0 mmol) in MeCN-H2O (10:1; 5 mL) was added N-iodosaccharin (1.5 mmol) at r.t. and the reaction mixture was allowed to stir for the time mentioned in Table
[1]
. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude mass was purified over SiO2 using hexane-EtOAc as eluent to furnish the pure glycosyl hemiacetal as an anomeric mixture. Products of all known compounds gave acceptable 1H NMR and 13C NMR spectra that matched the data reported in the cited references.
[28]
28 Spectral data of selected compounds:
3-
O
-Acetyl-4,6-
O
-benzylidene-2-deoxy-2-phthalimido-d
-glucopyranose (Table 1, Entry 13): 1H NMR (300 MHz, CDCl3): δ = 7.33-7.91 (m, 9 H, aromatic protons), 5.85 (t, J = 9.0 Hz, 1 H, H-3), 5.69 (d, J = 8.1 Hz, 1 H, H-1), 5.58 (s, 1 H, PhCH), 4.48 (dd, J = 4.5, 10.2 Hz, 1 H, H-4), 4.35-4.40 (m, 1 H, H-2), 3.70-3.83 (m, 3 H, H-5, H-6a, H-6b), 1.88 (s, 3 H, OCOMe). ESI-MS: m/z calcd for C23H21NO8: 439; found: 462 [M + Na]+.
2,3,4,5,6-Penta-
O
-acetyl-d
-galactose (Table 1, Entry 20): 1H NMR (300 MHz, CDCl3): δ = 2.04-2.12 (5 × s, 15 H), 3.91 (dd, 1 H), 4.26 (dd, 1 H), 5.26 (d, J = 2.0 Hz, 1 H), 5.36 (m, 1 H), 5.49 (d, J = 8.0 Hz, 1 H), 5.62 (d, J = 8.0 Hz, 1 H), 9.45 (br s, 1 H). ESI-MS: m/z calcd for C16H22O11: 390; found: 413 [M + Na]+.
