A Novel Glycoside Anomerization Catalyzed by Trimethylsilyl Bromide and Zinc Bromide in Combination

A novel glycoside anomerization occurred when trimethylsilyl bromide (TMSBr) and zinc bromide were utilized in combination as a catalyst. Treatment of β-glycosides with TMSBr and zinc bromide in the presence of alcohols afforded anomerized products in good yields.

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 39; no. 3; pp. 590 - 592
Main Authors HIGASHI, Kunio, NAKAYAMA, Kiyoshi, UOTO, Kouichi, SHIOYA, Emiko, KUSAMA, Tsuneo
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 1991
Pharmaceutical Soc Japan
Maruzen
Japan Science and Technology Agency
Subjects
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
glucosamine
glycoside anomerization
Lewis acid
Life Sciences & Biomedicine
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
trimethylsilyl halide
zinc halide
GLYCOSIDE ANOMERIZATION
GLUCOSAMINE
LEWIS ACID
DERIVATIVES
TRIMETHYLSILYL HALIDE
ZINC HALIDE
Lewis acid
Catalytic reaction
Anomerization
Oxygen heterocycle
Aminoglycoside
Zinc Halides
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Summary:A novel glycoside anomerization occurred when trimethylsilyl bromide (TMSBr) and zinc bromide were utilized in combination as a catalyst. Treatment of β-glycosides with TMSBr and zinc bromide in the presence of alcohols afforded anomerized products in good yields.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.39.590