3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE1,2-(METHYLORTHOACETATE)

White Solid

Methyl 2, 3, 4-triacetyl-α, β-glucopyranuronate (2) (12.0 g, 36 mmol) and trichloroacetonitrile (18 mL, 180 mmol) was stirred in dry CHTo a solution of hydroxyglucuronic ester C (11.1 g, 33.3 mmol) in CHA stirred solution of (3R, 4S, 5S, 6S)-2-hydroxy-6-(methoxycarbonyl)tetrahydro- 2H-pyran-3, 4, 5-triyl triacetate (3.00 g, 8.98 mmol) in CH2C12 (30 mL) was chargedwith trichloroacetonitrile (12.9 g, 89.8 mmol) and Cs2CO3 (1.40 g, 4.49 mmol) at room temperature. The reaction mixture was stirred at same temperature for 2 hours. When TLC analysis showed complete consumption of the starting material, the reaction mixture was diluted with CH2C12 (50 mL), washed with aqueous NaHCO3 solution (2 x 20 mL), water (20 mL) and brine (20 mL). The organic layer was dried over anhydrousNa2SO4 and was concentrated under reduced pressure to afford crude. The crude product was purified by column chromatography (20percent EtOAc/hexanes) to afford (2S, 3S, 4S, 5R, 6R)-2-(methoxycarbonyl)-6-(2, 2, 2-trichloro- 1 -iminoethoxy)tetrahydro2H-pyran-3, 4, 5-triyl triacetate (2.00 g, 48percent) as a colorless liquid.13.1 g compound 8 (39. 2 mmole) was dissolved in 80 ml dry dichloromethane. 20.0 ml TRICHLOROACETONITRILE (195.9 mmole) and 0.6 ml DBU (3.9 mmole) were added. The mixture was stirred for 24h at r. t. under argon. To the solution was added 3 g of fine silica, the mixture was stirred for 5 min. and filtered. The filtrate was concentrated under reduced pressure and purified with flash chromatography (Acros Silicagel 0.060-0. 200 mm) using pentane/ethyl acetate 75: 25. A white solid was obtained (15.0 g, 79percent yield), consisting of 100percent a form. 1H-NMR : (500MHZ, CDC13) : 5 (ppm): 8.73 (s, 1H), 6.64 (d, 3.6 HZ, 1H), 5.63 (dd ap. t, 10.1 Hz, 1H), 5.27 (dd ap. t, 10.1 Hz, 1H), 5.15 (dd, 10.1/3. 6 Hz, 1H), 4.50 (d, 10.1 Hz, 1H), 3.75 (s, 3H), 2.05 (m, 6H), 2.01 (s, 3H). 13C-NMR : (50MHz, CDC13) : 8 (ppm): 169.8, 169.7, 169.5, 167.2, 160.5, 92.6, 90.5, 70.5, 69.4, 69.1, 68.9, 53.1, 20.7, 20.5, 20.4. IR (film) : Q (CM) : 3320 (w), 2957 (w), 1756 (s), 1679 (m), 1439 (w), 1370 (m), 1287 (w), 1218 (s), 1150 (w), 1043 (s), 971 (m), 914 (w), 835 (w), 797 (m), 734 (w), 697 (w), 645 (w), 600 (w), 552 (w).

Intermediate for the synthesis of various glucuronide derivatives

Molecular Weight:478.7
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:10
Exact Mass:476.999629
Monoisotopic Mass:476.999629
Topological Polar Surface Area:148
Heavy Atom Count:29
Complexity:680
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes