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2005
Carbohydrates
U 0500
Synthesis of Glycosyl Phosphonates by Michael-Type Addition to 2-Nitroglycals.
An efficient and simple route to various glycosyl phosphonates by Michael addition
04- 200 —
of HPO(O-Me)2 to 2-nitroglycals is described. While at short reaction times (5 min)
both diastereomers are obtained, a base-catalyzed rearrangement at longer reaction
time (2 h) leads to the exclusive isolation of the more stable isomer. The nitro derivatives are easily transformed into the corresponding amines such as (VI). —
(PACHAMUTHU, K.; FIGUEROA-PEREZ, I.; ALI, I. A. I.; SCHMIDT*, R. R.;
Eur. J. Org. Chem. 2004, 19, 3959-3961; Fachbereich Chem., Univ. Konstanz,
D-78434 Konstanz, Germany; Eng.) — Kieslich
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