Sodium Hydroxide → HCID 9889037, compound

Participants

Reaction Steps

By the above procedure for glycosylation of 3,6-bis(hydroxymethyl)-1,2-dithiin but using methyl 3,4-diacetyl-1,2-dideoxy-D-arabinohexenopyranosyluronate instead of triacetyl D-glucal, the product obtained after work-up is 3,6-di[methyl 4-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyluronate]oxymethyl-1,2-dithiin (17B). This diacetate dimethyl ester (20 mg) dissolved in 1 mL of THF is treated with 3 mL of 0.1M aqueous NaOH, and the resulting solution is stirred at room temperature for three hours. The hydrolyzed product is extracted, the extract layers are combined and dried, and the solvent removed. After purification by silica gel chromatography, the product is 3,6-di[sodium 2,3-dideoxy-α-D-erythro-hex-2-enopyranosyluronate]oxymethyl-1,2-dithiin (8B).

Provenance & Evidence