anti-Addition [92% diastereoselectivity (d.s.)] of 2-trimethylsilylthiazole (2) to O,N-protected L-serinal (1) and deblocking the formyl group in the resulting adduct, leads to the (2S,3S)-2,4-dihydroxy-3-aminobutanal derivative (7), which serves as a precursor both to masked 4-amino-4-deoxy-L-ribose/L- arabinose and D-erythro-C<inf>20</inf>-sphingosine.
Stereoselective mono- and bis-homologation of L-serinal via 2-trimethylsilylthiazole addition. The thiazole route to amino L-sugars and D-erythro-sphingosines
DONDONI, Alessandro;FANTIN, Giancarlo;FOGAGNOLO, Marco;MEDICI, Alessandro
1988
Abstract
anti-Addition [92% diastereoselectivity (d.s.)] of 2-trimethylsilylthiazole (2) to O,N-protected L-serinal (1) and deblocking the formyl group in the resulting adduct, leads to the (2S,3S)-2,4-dihydroxy-3-aminobutanal derivative (7), which serves as a precursor both to masked 4-amino-4-deoxy-L-ribose/L- arabinose and D-erythro-CFile in questo prodotto:
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