Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines

A route to epimeric carbon-linked glycoglycines that exploits the stereoselective addition of 2-lithiofuran and 2-lithiothiazole to sugar nitrones has been described. The reaction occurs with opposite diastereofacial selectivity depending on whether the free nitrone or the diethyl aluminum chloride...

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Published in:Journal of organic chemistry 1997-08, Vol.62 (16), p.5484-5496
Main Authors: Dondoni, Alessandro, Junquera, Federico, Merchán, Francisco Luis, Merino, Pedro, Scherrmann, Marie-Christine, Tejero, Tomas
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cited_by cdi_FETCH-LOGICAL-a295t-7fb703438bb65baf6de6de43b6b77d83194705fb42e358d55f1718a4bbd4c7a33
cites cdi_FETCH-LOGICAL-a295t-7fb703438bb65baf6de6de43b6b77d83194705fb42e358d55f1718a4bbd4c7a33
container_end_page 5496
container_issue 16
container_start_page 5484
container_title Journal of organic chemistry
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creator Dondoni, Alessandro
Junquera, Federico
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description A route to epimeric carbon-linked glycoglycines that exploits the stereoselective addition of 2-lithiofuran and 2-lithiothiazole to sugar nitrones has been described. The reaction occurs with opposite diastereofacial selectivity depending on whether the free nitrone or the diethyl aluminum chloride precomplexed derivative is employed. The resulting furyl or thiazolyl hydroxylamines are dehydroxylated to amines by the action of titanium(III) chloride. From these compounds the amino acids are revealed by the oxidative cleavage of the furan ring or by the conversion of the thiazole into the formyl group and oxidation to carboxylic acid. Compounds have been prepared wherein the α-amino acid moiety is installed at C-4 and C-1 of furanoses (ribo, manno, xylo, and lyxo) and at C-5 and C-1 of a pyranose (galacto).
doi_str_mv 10.1021/jo970290a
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title Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines
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