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A NEW APPROACH TO THE SYNTHESIS OF GLYCOCONJUGATES
Schmidt, Richard R.
Schmidt, Richard R.
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Issue Date
1987
Submitted date
2023-04-26
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Abstract
1-0-Unsubstituted aldoses afford with trichloroacetonitrile under base catalysis 0-(glycosyl)trichloroacetimidates in high yields. Depending on the reaction conditions either 0-(a-glycosyl) or 0-(ßB-glycosyl)trichloroacetimidates may be obtained highly selectively or even exclusively. The extraordinary diastereoselectivity control is mainly due to stereoelectronic effects. The 0-(a- or B-glycosyl)trichloroacetimidates are stable compounds, which can be isolated easily, quite often as erystalline material. They may be stored for a long period of time. However, upon mild acid catalysis they become strong glycosylating agents. They have proven as versatile intermediates in complex glycosidation reactions with different nucleophiles (0-, S-, N-, and C-nucleophiles). The application of this methodology to the synthesis of glycosphingolipids, glycophospholipid type compounds, and to the synthesis of the tetrasaccharide of the core region of 0-glycoproteins is presented. In addition, the 0-(glycosyl)trichloroacetimidate based synthesis of the repeating unit of Neisseria meningitidis (Serogroup L) will be outlined. Halogenoses and heavy metal salt catalysis are not required in these procedures.
Citation
Chemical synthesis in molecular biology, 137 ff
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Book chapter
conference paper
conference paper
Language
en
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Series/Report no.
GBF Monographs, Vol. 8
ISSN
0930-4320
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Attribution-NonCommercial-ShareAlike 4.0 International