Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units |
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Authors: | Morii Yasuharu Matsuda Hiroko Ohara Keiichiro Hashimoto Masaru Miyairi Kazuo Okuno Toshikatsu |
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Institution: | Faculty of Agriculture and Life Science, Hirosaki University, 3 Bunkyo-Cho, Hirosaki, Aomori 036-8561, Japan. |
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Abstract: | Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent beta-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. |
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