5 5,6-アチリジノ糖および抗生物貭ノジリマイシンの合成
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概要
- 論文の詳細を見る
Some 6-azido-5-tosyloxy-hexofuranoses were treated with lithium aluminum hydride or with sodium borohydride/cobalt(II)tris-(α,α'-dipyridyl)bromide to yield the corresponding 5,6-epimines. Thus, 3-O-benzyl-5,6-dideoxy-5,6-epimino-1,2-O-isopropylidene-β-L-idofuranose (10), -α-D-glucofuranose (16), 5,6-dideoxy-5,6-epimino-1,2-O-isopropylidene-β-L-idofuranose (21), and methyl 2,3-di-O-benzyl-5,6-dideoxy-5,6-epimino-α-L-altrofuranoside (32) were synthesized and characterized as their acetates. It was also found that the hydroxyl function in the 3-position considerably affected formation of aziridine or displacement of 5-O-tosyloxy group. The N-acetates of these 5,6-epimines were unstable to acids and treatment with acetic acid easily afforded 6-acetoxy-5-acetamido-hexofuranoses under an attack of acetate ion in the terminal position. Thus, 17 was converted into 6-O-acetyl-5-acetamido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (39), which gave 5-amino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (40) on debenzylation and hydrolysis. Successive treatment of 40 by N- and O-trifluoroacetylation, followed by de-O-acetonation with acids and removal of the protecting group with bases resulted in its conversion, in a good yield, into Nojirimycin (1), a monosaccharide antibiotic produced by some strains of Streptomyces which is active against Sarcina lutea and Xanthomonas oryzae.
- 天然有機化合物討論会の論文
- 1968-09-20
著者
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佐伯 博道
Central Research Laboratories, Sankyo Co., Ltd.
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佐伯 博道
Central Research Laboratories Sankyo Co. Ltd.
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佐伯 博道
三共中研
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大木 英二
三共中研
関連論文
- Deoxysugar Synthesis. I. Lithium-ethylamine Reduction of Carbohydrate Phosphorodiamidates
- Synthesis of 3', 4'-Dideoxybutirosin A, Active against Butirosin Resistant Bacteria
- Deoxysugar Synthesis. III. Removal of Vicinal Mesyloxy Groups with Naphthalene-Sodium
- Selective O-Benzoylation in Aminoglycoside Antibiotics
- Deoxysugar Synthesis. II. Deoxygenations of Methyl 2,6-Dibenzyloxy-carbonylamino-2,6-dideoxy-α-D-glucopyranoside
- Syntheses of Neamine Derivatives and Their Antibacterial Activities
- An Alternate Synthesis of Leupeptins and Their Analogs
- 1 6,7-エピイミノヘプトーズの合成及びリンコサミンに関する合成研究
- Nitromethane-Condensation Reaction with 5-Aldehydes of Pentodialdofuranosides
- Syntheses of 2,3-Di-O-benzyl-α-L-arabino-pentodialdo-1,4-furanoside and Its β-Anomer
- Conversion of D-Glucofuranose to L-arabino-Hexofuranoside
- Syntheses of 5,6-Aziridino Sugars
- Benzylation of Carbohydrate Derivatives in Dimethyl Sulfoxide.
- Rearrangement of D-glucofuranoside to L-Arabino-hexofuranoside : Synthesis of 6-Deoxy-6-nitro-L-arabino-hexofuranoside through L-Arabino-pentodialdo-1,4-furanoside from D-Glucose or L-Arabinose
- 5 ロイペプチンおよびその同族体の合成研究
- Synthesis of N-Acetyllincosamine
- Synthesis of N-Acetyllincosamine
- Synthesis of 6,7-Dideoxy-6,7-epimino-1,2 : 3,4-di-O-isopropylidene-D (and L)-glycero-α-D-galacto-heptopyranose and Its Conversion into 6-Amino-6-deoxyheptose
- Effect of 3-Hydroxyl Group on 5,6-Epimine Formation in 1,2-O-Isopropylideneglucofuranose
- 5,6-Epimino-D-glucofuranose and Synthesis of Nojirimycin (5-Amino-5-deoxyglucose)
- Syntheses and Characterizations of 5,6-Epimino-L-altro-and -L-idofuranoses
- 5 5,6-アチリジノ糖および抗生物貭ノジリマイシンの合成
- Synthesis of Nojirimycin, D-Glucopiperidinose