2004
DOI: 10.1021/jo049406a
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Stereoselective Synthesis of α- and β-l-C-Fucosyl Aldehydes and Their Utility in the Assembly of C-Fucosides of Biological Relevance

Abstract: An efficient synthesis of O-benzylated derivatives of the title sugar aldehydes via thiazole addition to tri-O-benzyl-l-fuconolactone followed by highly stereoselective deoxygenation of the resulting thiazolylketose and thiazole to formyl transformation is described. Wittig olefination of these aldehydes with galactopyranose and glucopyranose 6-phosphoranes and reduction of the resulting alkenes afforded alpha- and beta-linked (1-->6)-L-C-fucosyl disaccharides, namely, beta-L-C-Fuc-(1-->6)-alpha-D-Gal, alpha-L… Show more

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Cited by 31 publications
(14 citation statements)
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“…Bulky substituents in the axial position on the anomeric carbon tend to promote this equilibration. As we have noted above, al-C-fucosides do not adopt the native 1 C 4 chair, [24] but recent results suggest that a-fucosylamide can do so.…”
Section: Nmr Spectroscopy Studies: Conformation Of 2 a And Inter-a C mentioning
confidence: 82%
See 1 more Smart Citation
“…Bulky substituents in the axial position on the anomeric carbon tend to promote this equilibration. As we have noted above, al-C-fucosides do not adopt the native 1 C 4 chair, [24] but recent results suggest that a-fucosylamide can do so.…”
Section: Nmr Spectroscopy Studies: Conformation Of 2 a And Inter-a C mentioning
confidence: 82%
“…However, the conformation of a-l-C-fucosides has been found to deviate significantly from the native 1 C 4 chair. [24] a-Glicosylamides, although difficult to synthesize, [25][26][27] have the advantage of being chemically stable and essentially unknown in Nature, [28] they are therefore likely not to be recognized by hydrolytic enzymes. The only a-fucosylamide reported so far was found to adopt the 1 C 4 chair conformation.…”
Section: Introductionmentioning
confidence: 99%
“…Modification of the linked carbon atom with one or two fluorine atoms has also been used to enhance the electronegativity of the bridging unit and further limit its conformational flexibility, yet retain the benefit of the metabolically stable C -glycoside [100,101,102]. C -Glycosides have been used in the glycomimetic design of numerous inhibitors, including sLe x [96], GM 4 ganglioside [103], galactopyranosides [104,105], mannopyranosides [105,106,107], fucopyranosides [105,108,109], and pseudoglycopeptides [106], among others.…”
Section: Glycomimetic Design—strategies To Improve Pharmacokineticmentioning
confidence: 99%
“…Earlier work in our laboratory demonstrated the synthetic utility of formyl and ethynyl Cglycosides as building blocks in C-disaccharide, C-cerebroside, and C-glycosyl amino acid synthesis. More recently we focused our efforts on the preparation of L-C-fucosyl aldehydes and demonstrated their utility as precursors to C-fucosyl-containing disaccharides, amino acids, and phenylhydroxy acetates 21 (Scheme 7). The synthesis of these aldehydes relied on our efficient thiazole-based methodology that exploits the synthetic equivalent of the thiazole ring with the formyl group.…”
Section: L-c-fucosyl Aldehydes and Ketonesmentioning
confidence: 99%