HCID 86725167, compound → HCID 71246010, compound

To a solution of protected rhamnoside 46 (145 mg, 0.19 mmol) in THF (4 ml) NaOMe (0.5 M in MeOH, 0.5 ml) was added and stirred for 4 h. The mixture was neutralized with Amberlite IR 120 (H+) ion exchange resin, filtered and concentrated. The crude product was dissolved in a mixture of THF (10 ml) MeOH (5 ml), H2O (4 ml) and AcOH (1 ml). The solution was purged with Ar, then 10% Pd/C (300 mg) was added and the solution purged with H2 for 30 min, then stirred under an H2 atmosphere for 12 h, filtered and concentrated. Purification by RP SPE (Waters Sep-Pak®, C18) afforded 39 (44 mg, 0.18 mmol, 94%). 1H-NMR (600 MHz, D2O) δ 4.85 (s, 1H, anomeric Rha), 4.01-3.96 (m, 1H), 3.81-3.70 (m, 3H), 3.62-3.57 (m, 1H), 3.50 (app. t, J=9.6, 1H), 3.11-3.03 (m, 2H), 1.78-1.67 (m, 4H, linker), 1.56-1.46 (m, 2H), 1.34 (d, J=6.3, 3H, Rha CH3)13C-NMR (150 MHz, D2O) δ 98.3 (anomeric), 70.6, 70.0, 68.8, 67.1, 66.1, 38.0, 26.6, 25.1, 21.0, 15.2 (Rha CH3); HRMS (MALDI-TOF): Calcd for C11H23NO5Na+ [M+Na]+ 272.1468. found 272.1433.

1. filtrationfiltered
2. concentrationconcentrated
3. dissolutionThe crude product was dissolved in a mixture of THF (10 ml) MeOH (5 ml), H2O (4 ml) and AcOH (1 ml)
4. customThe solution was purged with Ar
5. addition10% Pd/C (300 mg) was added
6. customthe solution purged with H2 for 30 min
7. stirringstirred under an H2 atmosphere for 12 h
8. filtrationfiltered
9. concentrationconcentrated
10. customPurification by RP SPE (Waters Sep-Pak®, C18)

ORD record

ord-841c639de9d64b22b014ff0646c164d3

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238669B2