The Chemistry of O-Silylated Ketene Acetals : Synthesis of N-Benzoyl-L-daunosamine

The Chemistry of O-Silylated Ketene Acetals : Synthesis of N-Benzoyl-L-daunosamine

N-Benzoyl-L-daunosamine was synthesized with high stereoselectivity utilizing a 1, 3-addition of ketene silyl acetal to the chiral nitrone, (Z)-[(4S, 5S)-2, 2, 5-trimethyl-1, 3-dixolan-4-yl]methylene[(1S)-1-phenylethyl]amine N-oxide, followed by a silyl group-transfer reaction in acetonitrile under...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1989/06/25, Vol.37(6), pp.1446-1451
Hauptverfasser: KITA, Yasuyuki, ITOH, Fumio, TAMURA, Osamu, KE, Ya Yuan, MIKI, Takashi, TAMURA, Yasumitsu
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
chiral nitrone
Condensed benzenic and aromatic compounds
diastereoselective 1, 3-addition
Exact sciences and technology
L-daunosamine
O-silylated ketene acetal
Organic chemistry
Preparations and properties
silyl group-transfer reaction
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Zusammenfassung:N-Benzoyl-L-daunosamine was synthesized with high stereoselectivity utilizing a 1, 3-addition of ketene silyl acetal to the chiral nitrone, (Z)-[(4S, 5S)-2, 2, 5-trimethyl-1, 3-dixolan-4-yl]methylene[(1S)-1-phenylethyl]amine N-oxide, followed by a silyl group-transfer reaction in acetonitrile under mild conditions.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.37.1446