Methanol → HCID 14826692, compound
Reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[N+:13]([CH3:16])([O-:15])=[O:14].[CH3:17][OH:18]>>[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@H:7]([C@H:9]([C@@H:11]([CH2:17][OH:18])[OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[N+:13]([CH2:16][C@@H:2]([C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])[OH:1])([O-:15])=[O:14]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-a879a7dd50964c27a238b8c9d2f242c8
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759070B2
Reaction notes
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