HCID 10842721, compound → HCID 53859827, compound

A solution of NaOMe (0.1 M, 0.6 mL) was added to a solution of 4k (See FIG. 7) (877 mg, 1.18 mmol) in MeOH (6 mL) under N2. After 3 hours, the reaction solution was passed through a Dowex 5OW(H+) plug (4×1 cm, eluant MeOH) and the solvent removed to give 2-bromoethyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside (4f) (See FIG. 7) (476 mg, 90%) as a white foam which was used directly in the next step. NaSSO2CH3 (185 mg, 1.38 mmol) was added to a solution of 4f (See FIG. 7) (476 mg, 1.06 mmol) in DMF (24 mL) under N2 and warmed to 50° C. After 21 hours, the solution was cooled and the solvent removed. The residue was purified by flash chromatography (CHCl3:MeOH: AcOH: H2O, 60:30:3:5) to give If (See FIG. 7) (346 mg, 68%) as a hygroscopic foam; [α]28D=+1.5 (c 1.66, H2O); IR (KBr) 3416 cm−1 (br, OH), 1311, 1131 cm−1 (S—SO2); 1H NMR (400 MHz, D2O, COSY) δ 3.10-3.13 (m, 1H, H-2), 3.30 (t, J6.0 Hz, 2H —CH2S—), 3.31 (dd, J1′,2′ 7.8 Hz, J2′,3′ 10.3 Hz, 1H, H-2′), 3.34 (s, 3H, CH3SO2—), 3.38-3.54 (m, 5H), 3.44 (dd, J2′,3′ 10.3 Hz, J3′,4′ 3.3 Hz, 1H, H-3′), 3.57 (dd, J8.4 Hz, J 11.4 Hz, 1H), 3.59 (dd, J4.9 Hz, J7.3 Hz, 1H), 3.70 (br d, J3′,4′ 3.3 Hz, 1H, H-4′), 3.77 (dd, J1.0 Hz, J11.5 Hz, 1H), 3.79-3.83 (m, 1H, —OCHH′—), 3.97-4.02 (m, 1H, —OCHH′—), 4.22 (d, J1′,2′ 7.8 Hz, 1H, H-1′), 4.33 (d, J1,2 7.8 Hz, 1H, H-1); 13C NMR (125 MHz, D2O) δ 36.7 (—CH2S—), 50.8 (CH3SO2—), 61.0, 62.1, 69.4, 69.6, 71.9, 73.5, 73.7, 75.3, 75.9, 76.4, 79.3 (—OCH2—, C-2, C-3, C-4, C-5, C-6, C-2′, C-3′, C-4′, C-5′, C-6′), 103.3, 103.9 (C-1, C-1′); HRMS m/z (FAB+): Found 503.0886 (M+Na+); C15H28O13S2Na requires 503.0869.

1. customthe solvent removed

ORD record

ord-4dd3e8228506426e879e89d61224efa4

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06512098B2