Glycosides. Part IV. 3,4,6-Tri-O-acetyl-2-O-benzyl-α-d-glucopyranosyl Bromide

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

“…This compound was obtained from 2,3,4,6-tetra-O-benzoyl-a-d-galactopyranosyl bromide (5) [24] by method A (KSTaz, [18] [81] by method A (NaSTaz, [15] (11) [25] by method A (KSTaz, acetone), cream foam, 71 % yield. Compound 12 was also obtained from 3,4,6-tri-Oacetyl-1,2-anhydro-a-d-glucopyranose (22) [29] by method C in 78 % yield.…”

Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation

“…AgNO 3 was added to a solution of 3,4,6-tri- O -acetyl-2- O -benzyl-α- d -glucopyranosyl bromide [39] (653.4 mg, 1.42 mmol) in dry acetonitrile (6.0 mL) and the resulting mixture was stirred for 5 min at room temp. After that, the solids were filtered off through a pad of Celite and the filtrate was concentrated under reduced pressure.…”

OFox imidates as versatile glycosyl donors for chemical glycosylation

“…14 Analytical data for 12 : R f = 0.43 (ethyl acetate/hexanes, 2/3, v/v); 1 H n.m.r. (300 MHz): δ , 1.96, 1.98, 2.00 (3s, 9H, 3 × COCH 3 ), 3.57 (dd, 1H, J 2,3 = 9.6 Hz, H-2), 4.12 (m, 1H, J 5,6a = 4.1 Hz, H-6a), 4.22 (m, 1H, H-5), 4.27 (dd, 1H, J 5,6b = 4.0 Hz, J 6a,6b = 12.6 Hz, 6b), 4.63 (dd, 2H, 2 J = 12.3 Hz, C H 2 Ph), 5.06 (dd, 1H, J 4,5 = 9.8 Hz, H-4), 5.48 (dd, 1H, J 3,4 = 9.5 Hz, H-3), 6.34 (d, 1H, J 1,2 = 3.9 Hz, H-1), 7.27–7.42 (m, 5H, aromatic) ppm; 13 C n.m.r.…”

“…We also demonstrated that thioglycoside 11 13 can be converted into OFox imidate 10 in 95% yield in the presence of N -iodosuccinimide (entry 6). The synthesis of 2-benzyl-3,4,6-tri- O -acetylated OFox imidate 13 was performed from the corresponding bromide 12 14 in 80% yield (entry 7). The formation of OFox imidates in all cases was confirmed by detecting changes in the 19 F NMR signals from −112.4 ppm for 3,3-difluoro-2-oxindole to −121 to −122 ppm for the coupled product.…”