Studies on Organic Fluorine Compounds. XLVII. Synthesis of Trifluoromethylated Sugars through the Aldol Reaction of 2-Trimethylsilyloxy-4-trifluoromethylfuran

KOSUKE SAWADA, Osamu Kitagawa, TAKEO TAGUCHI, YUJI HANZAWA, YOSHIRO KOBAYASHI, YOICHI IITAKA

研究成果: Article

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抄録

Lewis acid-catalyzed aldol condensation of 2-trimethylsilyloxy-4-trifluoromethylfuran (2a) with aldehydes was found to proceed in a regio- and diastereoselective manner to give the 5-substituted 4-trifluoromethyl-2 (5H)-furanone (4) in good yield. The aldol product (4a) derived from benzyloxyacetaldehyde was successfully converted to the branched sugar (12), the first reported example of a trifluoromethylated branched sugar, and its crystal structure was determined by X-ray analysis.
元の言語English
ページ(範囲)4216-4222
ジャーナルChemical and Pharmaceutical Bulletin
33
発行部数10
出版物ステータスPublished - 1985

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Fluorine Compounds
Sugars
Lewis Acids
X ray analysis
Aldehydes
Condensation
Crystal structure
3-hydroxybutanal

これを引用

Studies on Organic Fluorine Compounds. XLVII. Synthesis of Trifluoromethylated Sugars through the Aldol Reaction of 2-Trimethylsilyloxy-4-trifluoromethylfuran. / SAWADA, KOSUKE; Kitagawa, Osamu; TAGUCHI, TAKEO; HANZAWA, YUJI; KOBAYASHI, YOSHIRO; IITAKA, YOICHI.

:: Chemical and Pharmaceutical Bulletin, 巻 33, 番号 10, 1985, p. 4216-4222.

研究成果: Article

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abstract = "Lewis acid-catalyzed aldol condensation of 2-trimethylsilyloxy-4-trifluoromethylfuran (2a) with aldehydes was found to proceed in a regio- and diastereoselective manner to give the 5-substituted 4-trifluoromethyl-2 (5H)-furanone (4) in good yield. The aldol product (4a) derived from benzyloxyacetaldehyde was successfully converted to the branched sugar (12), the first reported example of a trifluoromethylated branched sugar, and its crystal structure was determined by X-ray analysis.",
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T1 - Studies on Organic Fluorine Compounds. XLVII. Synthesis of Trifluoromethylated Sugars through the Aldol Reaction of 2-Trimethylsilyloxy-4-trifluoromethylfuran

AU - SAWADA, KOSUKE

AU - Kitagawa, Osamu

AU - TAGUCHI, TAKEO

AU - HANZAWA, YUJI

AU - KOBAYASHI, YOSHIRO

AU - IITAKA, YOICHI

PY - 1985

Y1 - 1985

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AB - Lewis acid-catalyzed aldol condensation of 2-trimethylsilyloxy-4-trifluoromethylfuran (2a) with aldehydes was found to proceed in a regio- and diastereoselective manner to give the 5-substituted 4-trifluoromethyl-2 (5H)-furanone (4) in good yield. The aldol product (4a) derived from benzyloxyacetaldehyde was successfully converted to the branched sugar (12), the first reported example of a trifluoromethylated branched sugar, and its crystal structure was determined by X-ray analysis.

M3 - Article

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EP - 4222

JO - Chemical and Pharmaceutical Bulletin

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