HCID 10718565, compound → HCID 86583654, compound

Participants

Reaction Steps

A solution of NaOMe (0.1M, 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.

Provenance & Evidence