1984 Volume 48 Issue 7 Pages 1831-1834
Several analogs of stevioside were synthesized for an examination of their tastes. Hepta-O- acetylsteviolbioside was coupled with tri-0-acetyl-α-D-xylopyranosyl bromide, tri-O-acetyl-β-Larabinopyranosyl bromide, tetra-O-acetyl-α-D-mannopyranosyl bromide, tetra-O-acetyl-α-Lglucopyranosyl bromide, tri-O-acetyl-α-L-rhamnopyranosyl chloride and tri-(9-acetyl-α-Lquinovopyranosyl bromide, respectively, and the resulting coupling products were deacetylated to give 13-O-β-sophorosyl-steviol β-D-xylopyranosyl ester (2), 13-0-β-sophorosyl-steviol a-Larabinopyranosyl ester (3), 13-O-β-sophorosyl-steviol a-D-mannopyranosyl ester (4), 13-0-β- sophorosyl-steviol β-L-glucopyranosyl ester (5), 1 3-O-β-sophorosyl-steviol a-L-rhamnopyranosyl ester (6) and 13-O-β-sophorosyl-steviol β-L-quinovopyranosyl ester (7). Stevioside and 2 -7 were sweeter than sucrose by 255, 160, 285, 285, 210, 200, and 1 10 times on a weight basis, respectively.
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