Chemical Modification of Maltose. VII. Synthesis of 4-O-(2-Acetamido-2-deoxy-α-D-glucopyranosyl)-D-glucopyranose (GlcNAcα1→4Glc)

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概要

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• 1,6-Anhydro-2,3,3'-tri-O-benzyl-4', 6'-O-benzylidene-β-maltose (5), a maltose derivative having only one unprotected hydroxyl group at the C-2' position, was synthesized from 1,6-anhydro-4', 6'-O-benzylidene-2'-O-tosyl-β-maltose (2) by benzylation followed by removal of the tosyl group with base. Compound 5 was converted into the corresponding ulose (7) by dimethylsulfoxide (DMSO)-Ac_2O oxidation. Treatment of 7 with hydroxylamine gave the 2'-oxime (9). Reduction of 9 with LiAlH_4 in ether and subsequent N-acetylation gave protected 1,6-anhydro-β-N-acetyl-glucosaminylglucose (12) and -mannosaminylglucose (13) in a yield ratio of ca. 6 : 1. Debenzylidenation followed by debenzylation of 12 or 13 gave 1,6-anhydro-β-N-acetyl-glucosaminylglucose (17) or-mannosaminylglucose (19). The title sugar was obtained was white prisms by acetolysis of the 1,6-anhydro-β-linkage of peracetylated 17,followed by de-O-acetylation.

• 社団法人日本薬学会の論文
• 1983-05-25

著者

• 森 雅美

  金城学院大学薬学部

• 森 雅美

  名古屋市立大学看護学部(生化学)

• 森 雅美

  愛知きわみ看護短期大学

• 手島 節三

  名古屋市立大学薬学部

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 森 雅美

  Faculty of Pharmaceutical Sciences, Nagoya City University

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