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

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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.
Original languageEnglish
Pages (from-to)4216-4222
JournalChemical and Pharmaceutical Bulletin
Volume33
Issue number10
Publication statusPublished - 1985

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

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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.

In: Chemical and Pharmaceutical Bulletin, Vol. 33, No. 10, 1985, p. 4216-4222.

Research output: Contribution to journalArticle

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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

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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.

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