Novel and convergent synthesis of modified glycosphingolipids, galactosyl-5-aza-sphinganines, by a diversity-oriented method

The stereocontrolled synthesis of β-galactosyl-5-aza-sphinganines was accomplished with high efficiency by a novel and convergent strategy. The truncated β-galactosphinganine 5 was easily acylated with different long chains. Moreover, the simple conversion of thiazole to formyl enabled 5-aza-alkylch...

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Bibliographic Details
Published in:Tetrahedron 2011-07, Vol.67 (29), p.5176-5183
Main Authors: Roy, Bimalendu, Ferdjani, Salim, Tellier, Charles, Rabiller, Claude
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Conversion
Exact sciences and technology
Galactosidase
Glycolipids
Glycosphinganines
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Lipids
Organic chemistry
Preparations and properties
Reductive amination
Strategy
Synthesis (chemistry)
Tetrahedrons
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Summary:The stereocontrolled synthesis of β-galactosyl-5-aza-sphinganines was accomplished with high efficiency by a novel and convergent strategy. The truncated β-galactosphinganine 5 was easily acylated with different long chains. Moreover, the simple conversion of thiazole to formyl enabled 5-aza-alkylchains to be introduced via an amino-reduction reaction. The overall yield for the synthesis of β-galacto-5-aza-sphinganines 9 and 13 was about 30–35% starting from 5. Preliminary results concerning the β-transgalactosylation of a truncated sphinganine catalyzed by galactosidases are also presented and discussed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.05.054