Synthesis of Fluorescent 4-Methyl-7-thiocoumaryl S-Glycosides of Sialic Acid

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概要

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• Condensation of 4-methyl-7-thiocoumarin sodium salt with methyl 5-N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonulopyranosonate (2), methyl 5-N-(O-acetylglycolyl)-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,6-trideoxy-D-glycero-D-galacto-2-nonulopyranosonate (11), and methyl 4,5,7,8,9-penta-O-acetyl-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (14) under Williamson reaction conditions gave the corresponding α-glycosides in good yields. Deprotection of these α-glycosides gave three new fluorogenic substrates, the 4-methylcoumarin-7-yl S-glycosides of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-D-glucose-D-galacto-2-nonulopyranosonic acid (KDN). Furthermore, we have developed a facile method for preparation of benzyl 5-amino-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosidonic acid (7), a key intermediate for the synthesis of N-glycolylneuraminic acid.

• 公益社団法人日本薬学会の論文
• 1995-11-15

著者

• 田中 正一

  Graduate School Of Pharmaceutical Sciences Kyushu University

• 古畑 公夫

  School of Pharmaceutical Sciences, Kitasato University

• 高柳 弘明

  School of Pharmaceutical Sciences, Kitasato University

• 高柳 弘明

  北里大・薬

• 古畑 公夫

  北里大薬

• 高柳 弘明

  北里大学薬学部薬化学教室

• 高柳 弘明

  School Of Pharmaceutical Sciences Kitasato University

• 孫 学龍

  Shenyang Pharmaceutical University

• Sun Xue-long

  School Of Pharmaceutical Sciences Kitasato University

• 田中 誠

  School Of Pharmaceutical Sciences Kitasato University

• 孫 学龍

  School of Pharmaceutical Sciences, Kitasato University

• 甲斐 俊次

  School of Pharmaceutical Sciences, Kitasato University

• 宇田 裕

  Department of Health Chemistry, Niigata College of Pharmacy

• 宇田 裕

  Department Of Health Chemistry Niigata College Of Pharmacy

• 甲斐 俊次

  School Of Pharmaceutical Sciences Kitasato University

• Sun X‐l

  Shenyang Pharmaceutical University

関連論文

• Studies on Sialic Acids. XIV. Lactone Derivatives of N-Acetylneuraminic Acid
• Studies on Sialic Acids. VII. : The Crystal and Molecular Structure of N-Acetyl-2,3-dehydro-2-deoxyneuraminic Acid
• Studies on Sialic Acids. XI. : Synthesis of 2-O-Clycosyl Derivatives of N-Acetylneuraminic Acid
• Synthesis of 2-(5-Cholesten-3β-yloxy) Glycosides of N-Acetyl-D-neuraminic Acid Derivatives(Organic,Chemical)
• Studies on Sialic Acids. XXV. Synthesis of the α- and β-N-Glycosides of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN)
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