Methanol → HCID 14826692, compound

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Reaction Steps

The heptose was prepared by the condensation of D-galactose with nitromethane in alkaline methanol. The crystalline 1-deoxy-1-nitro-D-glycero-L-manno-heptitol obtained from the aqueous solution of the deionized products (mp 158° C., 21% yield) was converted to its sodium salt. On treatment with dilute sulphuric acid (35° C.), followed by deionization with Rexyn 101(H+) and Amberlite A4(OH−) ion-exchange resins, the solution was lyophilized to give the heptose as a syrup (80% yield). The product was fractionated by cellulose column chromatography using butan-1-ol-water (1:10 v/v) as the eluant. Fractions containing the heptose were concentrated to dryness under reduced pressure. The D-glycero-L-manno-heptose having [α]D −14° (c 0.2, water) was pure by paper chromatography and its reduced (NaBH4) and acetylated product on GLC gave a single peak corresponding in retention time with that of authentic hepta-O-acetyl-D-glycero-L-manno-heptitol, establishing its purity.

Provenance & Evidence