A Preparation of the Branched Trisaccharide 2-Acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-3-O-(β-D-xylopyranosyl)-D-glucopyranose (3-O-β-D-Xylopyranosyl-N-acetyllactosamine)

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概要

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• The title branched trisaccharide (19) was prepared from benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (1) by stepwise Koenigs-Knorr condensation followed by removal of the protecting groups. Benzyl 2-acetamido-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-2-deoxy-α-D-glucopyranoside (4), prepared by coupling 1 with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide followed by debenzylidenation, is a key intermediate in this preparation. Removal of the benzyl and O-acetyl groups of 4 gave a crystalline 2-acetamido-2-deoxy-3-O-(β-D-xylopyranosyl)-α-D-glucopyranose. Preferential etherification and esterification of 4 were investigated. Selective benzylation of 4 afforded the 6-O-benzoate (15). Condensation of 15 with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide provided a crystalline, protected trisaccharide in 41% yield, from which 19 was obtained as a white powder after removal of the protecting groups. Purified β-galactosidase from jack bean did not act on the β-galactosidic linkage in 19.

• 社団法人日本薬学会の論文
• 1980-01-25

著者

• 石原 英子

  名古屋市立大学看護短期大学部

• 石原 英子

  名古屋市立大学

• 手島 節三

  名古屋市立大学薬学部

• 小栗 重行

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 石原 英子

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 小栗 重行

  Faculty Of Pharmaceutical Sciences Nagoya City University

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