Selective Synthesis of α-C-(Alkynyl)-galactosides by an Efficient Tandem Reaction

Several α-C-(alkynyl)-galactosides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.

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Bibliographic Details
Published in:Journal of organic chemistry 2006-02, Vol.71 (3), p.1015-1017
Main Authors: Guillarme, Stéphane, Plé, Karen, Haudrechy, Arnaud
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Galactosides - chemical synthesis
Galactosides - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Zinc - chemistry
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Description
Summary:Several α-C-(alkynyl)-galactosides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0519817