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      Synthesis of the alpha-D-GlcpA-(1-->3)-alpha-L-Rhap-(1-->2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris.

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      Carbohydrate research

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          Abstract

          The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplén deacetylation of the trisaccharide 12 resulted in the 6"-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).

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          Author and article information

          Journal
          Carbohydr. Res.
          Carbohydrate research
          0008-6215
          0008-6215
          Sep 07 2001
          : 334
          : 4
          Affiliations
          [1 ] Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 55, H-4010, Debrecen, Hungary.
          Article
          S0008621501001963
          11527526

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