Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220985 | Tetrahedron | 2011 | 8 Pages |
Abstract
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.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Bimalendu Roy, Salim Ferdjani, Charles Tellier, Claude Rabiller,