A Novel Glycosidation Promoted by the Combination of Trimethylsilyl Halide and Zinc Triflate

• Published in: Chemical & pharmaceutical bulletin Vol. 40; no. 8; pp. 2019 - 2022
• Main Authors: HIGASHI, Kunio, SUSAKI, Hiroshi
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 1992; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: activator; alkyl glycoside; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Exact sciences and technology; glycosaminyl acetate; glycosidation; glycosyl donor; glycosyl ester; Life Sciences & Biomedicine; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; steroidal glycoside; trimethylsilyl bromide; trimethylsilyl chloride; zinc triflate; ZINC TRIFLATE; TRITYL PERCHLORATE; PENTENYL GLYCOSIDES; EFFICIENT SYNTHESIS; GLYCOSYL ESTER; GLYCOSYL DONOR; PENT-4-ENYL GLYCOSIDES; HIGHLY STEREOSELECTIVE GLYCOSYLATION; GLYCOSAMINYL ACETATE; TRIMETHYLSILYL CHLORIDE; SILVER PERCHLORATE; ACTIVATOR; ALKYL GLYCOSIDE; FACILE SYNTHESIS; ALPHA-GLUCOSIDES; CATALYST SYSTEM; TRIMETHYLSILYL BROMIDE; GLYCOSIDATION; STEREOCONTROLLED SYNTHESIS; STEROIDAL GLYCOSIDE; Steroid; Stereoselectivity; Catalytic reaction; Aldose; Aliphatic compound; Medium effect; Aminoglycoside; Glycoside; Secondary alcohol; Primary alcohol
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.40.2019

A novel glycosidation method has been developed which utilizes a trimethylsilyl halide-zinc triflate catalyst system to activate various benzyl-protected fucosyl, glucosyl and galactosyl esters. The promoter system was extended to use benzyl-protected alkyl glycosides and N-2, 2, 2, -trichloroethoxycarbonyl-protected glucosaminyl and galactosaminyl acetates as glycosyl donors.