Silver Imidazolate-assisted Glycosidation. Part 3. Synthesis of alpha-D-Glucopyranosides and alpha-D-Galactopyranosides.

Glycosyl Disulfides: Novel Glycosylating Reagents with Flexible Aglycon Alteration

“…Data for β- 13a : [α] 26.1 D +7.9 ( c 0.5, CHCl 3 ); IR (thin film) 3063, 3030 (Ar C−H), 2985 (C−H) cm -1 ; 1 H NMR (500 MHz, CDCl 3 ) δ 3.31 (t, 1H, H-2‘, J (H-2‘,H-1‘) = 8.3 Hz), 3.34−3.38 (m, 1H, H-5‘), 3.55−3.58 (m, 2H, H-3‘, H-4‘), 3.64 (d, 2H, H-6‘, J (H-6‘,H-5‘) = 2.9 Hz), 4.00 (d, 2H, H-6, J (H-6,H-5) = 6.2 Hz), 4.27 (d, 1H, H-3, J (H-3,H-4) = 3.1 Hz), 4.31 (dd, 1H, H-4, J (H-4,H-5) = 4.4 Hz, J (H-4,H-3) = 2.8 Hz), 4.37 (dt, 1H, H-5, J (H-5,H-6) = 6.2 Hz, J (H-5,H-4) = 4.6 Hz), 4.39 (d, 1H, H-1‘, J = 7.9 Hz), 4.42 (d, 1H, H-2, J (H-2,H-1) = 3.8 Hz), 4.48 (d, 1H, PhC H H‘, J = 12.3 Hz), 4.51 (d, 1H, PhC H H‘, J = 12.1 Hz), 4.55 (d, 1H, PhCH H ‘, J = 12.0 Hz), 4.66 (s, 2H, PhC H 2 ), 4.74 (d, 1H, PhCH H ‘, J = 10.8 Hz), 4.75 (d, 1H, PhC H H‘, J = 11.00 Hz), 4.83 (d, 1H, PhCH H ‘, J = 11.00 Hz), 5.70 (d, 1H, H-1, J (H-1,H-2) = 3.8 Hz), 7.03−7.14, 7.16−7.33 (m, 20H, Ar- H ); 13 C NMR (125 MHz, CDCl 3 , HSQC) δ 25.3, 26.1, 26.5, 26.7 ( C H 3 ), 65.8 (C-6), 68.5 (C-6‘), 73.5 (Ph C H 2 ), 73.6 (C-5), 75.0 (Ph C H 2 ), 75.1 (Ph C H 2 ), 75.4 (Ph C H 2 ), 75.7 (C-5‘), 77.6 (C-3‘ or C-4‘), 80.2 (C-3 and C-4), 82.1 (C-2‘), 82.6 (C-2), 84.6 (C-3‘ or C-4‘), 101.3 (C-1‘), 105.1 (C-1), 108.5, 111.8 ((CH 3 ) 2 C ), 127.89, 127.92, 128.01, 128.09, 128.29, 128.64, 128.66, 128.69, 128.74 (Ar- C H), 138.23, 138.37, 138.45, 138.70 (Ar- C ); MS−ES + m / z (%) 805.3 (100) (M + + Na), 503.2 (95). The spectroscopic and analytical data were in agreement with those reported in the literature. , …”