Studies on the Oxidation of "Reversed Nucleosides" in Oxygen. IV. Synthesis of 4-(6-Aminopurin-9H-9-yl)-3(R)-hydroxy-2(R)-aminobutyric Acid

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概要

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• Reaction of 5-O-tosyl-3-benzyloxycarbonylamido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (21) or 5-O-tosyl-3-acetamido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (30) with the sodium salt of adenine afforded the corresponding isomeric "reversed nucleosides" in good yields. Hydrolysis of the masked compound (22) followed by hydrogenolysis afforded 5-(6-aminopurin-9H-9-yl)-3-amino-3,5-dideoxy-D-ribofuranose (26) hydrochloride in a good yield. After removal of the protective group, oxidation of 5-(6-aminopurin-9H-9-yl)-3-acetamido-3,5-dideoxy-D-ribofuranose (33) by oxygen in a dilute alkaline solution afforded sodium 4-(6-aminopurin-9H-9-yl)-3(R)-hydroxy-2(R)-acetamidobutyrate (34). To evaluate the biological activities, amino ester (35) and amino acid (38) were also synthesized.

• 公益社団法人日本薬学会の論文
• 1974-12-25

著者

• 菅野 毅

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 河津 光高

  Organic Chemistry Research Laboratory of Tanabe Seiyaku Co., Ltd.

• 河津 光高

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

関連論文

• Studies on the Synthesis of Some Pyrrolocoumarins and Furoquinolones
• Studies on the Oxidation of "Reversed Nucleosides" in Oxygen. IV. Synthesis of 4-(6-Aminopurin-9H-9-yl)-3(R)-hydroxy-2(R)-aminobutyric Acid
• Studies on the Oxidation of "Reversed Nucleosides" in Oxygen. III. Synthesis of Eritadenine Analogues of Purines and Pyrimidines

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