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

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 language	English
Pages (from-to)	4216-4222
Journal	Chemical and Pharmaceutical Bulletin
Volume	33
Issue number	10
Publication status	Published - 1985

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

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.",

author = "KOSUKE SAWADA and Osamu Kitagawa and TAKEO TAGUCHI and YUJI HANZAWA and YOSHIRO KOBAYASHI and YOICHI IITAKA",

year = "1985",

language = "English",

volume = "33",

pages = "4216--4222",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "10",

}

TY - JOUR

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

N2 - 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.

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

SN - 0009-2363

VL - 33

SP - 4216

EP - 4222

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 10

ER -

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

Abstract

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