28 Daunosamineの合成

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概要

• 論文の詳細を見る

• Isomerization of methyl 2-thio-hexopyranoside derivatives in methanol to furanoside configurations by acid-catalyzed reaction was applied to the synthesis of daunosamine(3-amino-2,3,6-trideoxy-L-lyxo-hexose)(1) which is a component of the antibiotic Dauno-mycin. Methyl 3-azido-2-s-benzyl-3-deoxy-2-thio-α-D-altropyranoside(3) in methanol was transformed into the corresponding furanoside; methyl 3-azido-2-s-benzyl-3-deoxy-2-thio-α(andβ)-D-altrofuranoside (4a) by catalytic reaction of Amberlite CG120(H^+). Partial benzoy-lation of 4a gave 6-O-benzoyl derivatives(4b), the 5-O-p-toluene sulfonyl derivative of which was led to methyl 5,6-anhydro-3-azido-2-s-benzyl-3-deoxy-2-thio-α(andβ)-L-galactofuranoside(7) by epoxy-dation with methanolic sodium methoxide. Further, the 3-amino-3,6-dideoxy sugar(8a) was obtained from the reduction of 7 with LiAlH_4. Treatment of 8a with Raney Ni gave methyl 3-amino-2,3,6-trideoxy-α(andβ)-L-lyxo-furanoside(9) which was finally hydrolyzed to give 1 as the hydrochloride salt.

• 天然有機化合物討論会の論文
• 1973-10-01

著者

• 山口 忠敏

  Faculty Of Pharmaceutical Sciences Kyushu University:(present Address)department Of Hygiene Miyazaki

• 山口 忠敏

  九大薬

• 小嶋 正治

  九大薬

関連論文

• Thiosugars. VII. Synthesis of Methyl 2,3,5,6-Tetradeoxy-2,3,5,6-tetrathio-β-L-galactofuranoside and -a-D-Altrofuranoside
• Thiosugars(第2報)2,3-Dithiohexopyranoside類のFuranosideへの異性化反応
• Synthesis of Radioiodinated Analog of Oxazolidine-2,4-dione
• Thiosugars. IV. 2,3-Dideoxy-2,3-epithio-D-allose and 2,3-Dideoxy-2,3-epithio-D-mannose
• 28 Daunosamineの合成

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