Volume 20, Issue 22
Natural Products
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ChemInform Abstract: Nitro Compounds. Part 2. 3-Nitrobutanal, a New Building Block in the Synthesis of Methyl-Branched Carbohydrates.

R. + OEHRLEIN

R. + OEHRLEIN

Inst. Org. Chem., Univ., D-8700 Wuerzburg

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V. + JAEGER

V. + JAEGER

Inst. Org. Chem., Univ., D-8700 Wuerzburg

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First published: May 30, 1989

Abstract

Treatment of crotonaldehyde (I) with sodium nitrite (II) in an acidic solution gives the unstable 3-nitrobutanal (III), isolated as the acetal (V) or the silyl nitronate (VII).

ChemInform Abstract

Treatment of crotonaldehyde (I) with sodium nitrite (II) in an acidic solution gives the unstable 3-nitrobutanal (III), isolated as the acetal (V) or the silyl nitronate (VII). These are coupled with the aldehydes (VIII) or (X), forming the adducts (IX) or (XI) - (XIII). Methanolysis of (XI) yields the geminal nitromethylglycosides (XV) - (XVII).

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