Efficient synthesis of ethisterone glycoconjugate via bis-triazole linkage

[Display omitted] •Sugar based triazolyl azido-alcohols were prepared under one pot methodology.•Syntheses of bis-triazolyl ethisterone glycoconjugates were carried out from sugar based triazolyl azido-alcohols via CuAAC reaction.•The structures were established by FT-IR, NMR, and HR-MS analyses. Sy...

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Bibliographic Details
Published in:Carbohydrate research 2014-11, Vol.399, p.2-7
Main Authors: Mishra, Kunj B., Mishra, Bhuwan B., Tiwari, Vinod K.
Format: Article
Language:English
Subjects:
Carbohydrates
Click chemistry
Ethisterone - chemical synthesis
Ethisterone - chemistry
Glycoconjugates
Glycoconjugates - chemical synthesis
Glycoconjugates - chemistry
Molecular Conformation
Steroids
Triazoles - chemistry
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Summary:[Display omitted] •Sugar based triazolyl azido-alcohols were prepared under one pot methodology.•Syntheses of bis-triazolyl ethisterone glycoconjugates were carried out from sugar based triazolyl azido-alcohols via CuAAC reaction.•The structures were established by FT-IR, NMR, and HR-MS analyses. Synthesis of sugar based triazolyl azido-alcohols was accomplished via one pot click reaction of glycosyl alkynes with epichlorohydrin in aqueous medium. All the developed triazolyl azido-alcohols were further utilized for the synthesis of bis-triazolyl ethisterone glycoconjugates using CuAAC reaction. The developed triazole-linked ethisterone glycoconjugates would be crucial in androgen receptor pharmacology and chemical biology.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2014.09.001