HCID 10718565, compound → HCID 86583654, compound

A solution of NaOMe (0.1 M, 0.3 mL) was added to a suspension of 4g (See FIG. 6) (300 mg, 0.66 mmol) in MeOH (3 mL) under N2 and stirred vigorously. After 6 hours, the resulting solution was passed through a Dowex 50W(H+) plug (2×1 cm, eluant MeOH) and the solvent removed to give 2-bromoethyl α-D-glucopyranoside bromide (4b) (See FIG. 6) (178 mg, 94%) (The synthesis of 4b as an intermediate has been described previously. However, this method gave only a poor yield of product. Nagai et al., Carbohydr. Res., 190:165-180 (1989), which is hereby incorporated by reference) as a white solid. NaSSO2CH3 (100 mg, 0.75 mmol) was added to a solution of 4b (See FIG. 6) (178 mg, 0.62 mmol) in DMF (7 mL) under N2 and warmed to 50° C. After 25 hours, the solution was cooled and the solvent removed. The residue was purified by flash chromatography (MeOH:EtOAc, 1:9) to give 1b (See FIG. 6) (144 mg, 73%) as a hygroscopic foam; [α]27D=+109.9 (c 1.11, H2O); IR (film) 3423 cm−1 (OH), 1309, 1128 cm−1 (S—SO2); 1H NMR (500 MHz, D2O, COSY) δ 3.16 (t, J9.5 Hz, 1H, H-4), 3.28 (t, J5.9 Hz, 2H, —CH2S—), 3.30 (s, 3H, CH3SO2—), 3.31 (dd, J1,2 3.8 Hz, J2,3 9.9 Hz, 1H, H-2), 3.44 (t, J9.5 Hz, 1H, H-3), 3.47-3.53 (m, 2H, H-6, H-6′), 3.58-3.61 (m, 1H, H-5), 3.62 (dt, Jt 5.4 Hz, Jd 10.8 Hz, 1H, —OCHH′—), 3.79 (dt, Jt 6.3 Hz, Jd 10.8 Hz, 1H, —OCHH′), 4.72 (d, J1,2 3.8 Hz, 1H, H-1); 13C NMR (100 MHz, D2O) δ 36.7 (—CH2S—), 50.7 (CH3SO2—), 61.5 (—OCH2—), 67.2, 70.5, 72.3, 73.2, 74.0 (C-2, C-3, C-4, C-5, C-6), 99.4 (C-1); HRMS m/z (FAB+): Found 319.0517 (M+H+); C9H19O8S2 requires 319.0521.

1. customthe solvent removed

ORD record

ord-d657c482d43746eda112d9ea8e8a8f56

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06512098B2