Abstract:
3-Azido-3-deoxy-1,2-0-isopropylidene-a-D-allofuranose (6) was synthesised through a sequential series of reactions. 3- Azido-3-deoxy-1,2-0-isopropylidene-a-isopropylidene-α-D- xylopentadialdo-1,4-furanose (7) was prepared and converted into α— and β —isomers (10a+ 10b) of 3-azido-3-de0xymethyl xylopyranoside in quantitative yields. Selective tosylation of compound (10a) afforded two major products (II) and (11a). The compound (II) was converted to 4-0-benzy1-3-azido-3-deoxy-2-0-tosyl-α-D-methyl-xylopyranoside and eventually reduced to a crystalline product (13) in a quantitative yield. This underwent a change in the configuration to yield 4-0- benzyl-2, 3-epimino-deoxy-α-D-methyl lyxopyranoside (14) in 63% yield. The structures of all the products were characterised by infrared and 1H nmr parameters. Silica gel column chromatography was applied for the purification of the above compounds.
Page(s):
235-239
DOI:
DOI not available
Published:
Journal: Science International, Volume: 4, Issue: 3, Year: 1992