Synthesis of hybrids of d-glucose and d-galactose with 1-deoxynojirimycin analogues using ring-closing metathesis

Synthesis of Hybrids of D‐Glucose and D‐Galactose with Pyrrolidine‐Based Iminosugars as Glycosidase Inhibitors

“…Recently, design and synthesis of hybrid molecules have gained importance as they could be useful in improving or altering the properties of pharmaceutically important molecules 10. As part of our ongoing programme towards the design and synthesis and biological evaluation of iminosugars11a,11b including hybrid sugars11c–11f as glycosidase inhibitors, in this paper we wish to report the synthesis and biological evaluation of the hybrid molecules 6 – 9 derivedthrough domain integration of pyrrolidine‐based iminosugars: 1,4‐dideoxy‐1,4‐imino‐ L ‐xylitol 4 ,12 1,4‐dideoxy‐1,4‐imino‐ L ‐lyxitol 5 ,13 and sugar entities.…”

Recent developments in design and synthesis of bicyclic azasugars, carbasugars and related molecules as glycosidase inhibitors

“…Several hybrids of a sugar (D-glucose and D-galactose) and a six membered or a seven membered azasugar have been synthesized 46 starting from 3-nitro olefins 184, 185, and 192 as shown in Scheme 22. Thus, vinyl magnesium bromide addition on the conjugated nitro olefins 184 and 185 gave the corresponding 2-vinyl sugars which upon reduction of the nitro group followed by allylation of the protected amine gave 186 and 187 respectively.…”

Synthesis of sugar-derived spiroaminals via lactamization and metathesis reactions

“…R f : 0.4 (hexane-ethyl acetate, 9 : 1), [a] 28 D = +59.5 (c 2.0, CH 2 Cl 2 ). IR (neat) n max : 3088, 3063, 2920, 2867, 2118, 1724, 1659, 1605, 1435, 1273, 1101, 982, 736, (d,1H,J = 11.6 Hz,PhCH), 4.49-4.41 (ABq, 2H, J = 11.7 Hz, PhCH 2 ), 4.01-3.93 (m, 3H), 3.90 (dd, 1H, J = 2.4, 9.6 Hz), 3.69 (s, 3H, -OCH 3 ), 3.59 (dd, 1H, J = 7.6, 9.3 Hz), 3.54 (dd, 1H, J = 5.8, 9.3 Hz), 2.84 (ddd, 1H, J = 1.7, 7.2, 9.3 Hz, C(H a Hb) CHCO 2 Me), 2.71 (ddd, 1H, J = 1.4, 7.5, 8.9 Hz, C(HaH b ) CHCO 2 Me). 13 C NMR (125 MHz, CDCl 3 ) : d 166.3,141.6,138.8,138.1,137.9,137.9,124.9,93.8,81.0,78.3,75.6,74.5,73.9,73.6,72.6,72.5,68.3,51.6,38.6 (125 mg).…”

“…IR (neat) n max : 3220, 3063, 2923, 2854, 1669, 1496, 1453, 1363, 1085, 735, 698 cm -1 . 1 H NMR (500 MHz, CDCl 3 ): d 7.34-7.16 (m, 20H, Ar-H), 6.48 (s, 1H, -NH), 4.93 (d,1H,J = 11.3,PhCH). 4.87-4.79 (m, 3H, 3 ¥ PhCH), 4.68 (d,1H,J = 11.3 Hz,PhCH), 4.60-4.57 (m, 2H, 2 ¥ PhCH), 4.50 (d, 1H, J = 12.0 Hz, PhCH), 3.77-3.70 (m, 3H), 3.63-3.59 (m, 2H), 3.45 (d, 1H, J = 9.2), 2.47-2.43 (m, 1H), 2.32-2.25 (m, 1H), 2.12-2.09 (m, 1H), 1.87 (dt, 1H, J = 4.4, 13.0), 1.76-1.68 (m, 2H).…”

“…1 H NMR (500 MHz, CDCl 3 ): d 7.34-7.16 (m, 20H, Ar-H), 6.48 (s, 1H, -NH), 4.93 (d,1H,J = 11.3,PhCH). 4.87-4.79 (m, 3H, 3 ¥ PhCH), 4.68 (d,1H,J = 11.3 Hz,PhCH), 4.60-4.57 (m, 2H, 2 ¥ PhCH), 4.50 (d, 1H, J = 12.0 Hz, PhCH), 3.77-3.70 (m, 3H), 3.63-3.59 (m, 2H), 3.45 (d, 1H, J = 9.2), 2.47-2.43 (m, 1H), 2.32-2.25 (m, 1H), 2.12-2.09 (m, 1H), 1.87 (dt, 1H, J = 4.4, 13.0), 1.76-1.68 (m, 2H). 13 C NMR (125 MHz, CDCl 3 ) : d 173.5,138.0,137.7,85.9,82.9,82.0,78.0,75.6,74.7,73.3,71.3,68.5,31.6,30.9,15.7 d 172.9,138.7,137.9,137.6,87.4,84.4,83.0,77.9,75.6,75.0,73.6,73.0,68.9,31.7,22.6,15.6…”