Synthesis of p-nitrophenyl 6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-α-d-mannopyranoside |
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Authors: | Surjit S Rana Joseph J Barlow Khushi L Matta |
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Institution: | Department of Gynecology, Roswell Park Memorial institute, Buffalo, NY 14263 U.S.A. |
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Abstract: | The reaction of p-nitrophenyl 2,3-O-isopropylidene-α-d-mannopyranoside and 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-glucopyrano)-2,1-d]-2-oxazoline gave a crystalline, 6-O-substituted disaccharide derivative which, on de-isopropylidenation followed by saponification, produced the disaccharide p-nitrophenyl 6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-α-d-mannopyranoside. Synthesis of methyl 6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-α-d-mannopyranoside was also accomplished by a similar reaction-sequence. The structures of these disaccharides have been established by 13C-n.m.r. spectroscopy. |
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Keywords: | To whom correspondence should be addressed |
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