2-Nitroethanol, syntheses with

Thus, the 2-nitroethanol synthesis results in the addition of two carbon atoms to an aldose sugar to produce two higher-carbon ketose sugars epimeric at carbon 3. While the synthesis is general in nature, the two ketoses produced from any one aldose are seldom as readily separable as is fortunately the case with D-mannoheptulose and D-gluco-heptulose. However, the newly developed techniques of adsorption and partition chromatography will undoubtedly be of service for the more difficult separations. 

The reaction of a -halocarboxylic acids with sodium nitrite has been used to synthesize ni-tromethane, nitroethane and nitropropane, although the reaction fails for higher nitroalkanes. " A number of other reactions have been reported which use nitrite anion as a nucleophile, including (1) reaction of alkyl halides with potassium nitrite in the presence of 18-crown-6, (2) reaction of alkyl halides with nitrite anion bound to amberlite resins, (3) synthesis of 2-nitroethanol from the acid-catalyzed ring opening of ethylene oxide with sodium nitrite, and (4) reaction of primary alkyl chlorides with sodium nitrite in the presence of sodium iodide. ... 

The jyn-selective asymmetric nitroaldol reaction was successfully applied to the catalytic, asymmetric synthesis of ftireo-dihydrosphingosine (94), which elicits a variety of cellular responses by inhibiting protein kinase C (Figure 22).44 The nitroaldol reaction of hexadecanal 92 with 3 equiv. of nitroethanol (86) in the... 

Nitroethanol was recently employed as C/O bis-nucleophile by Hayashi and coworkers [38] for the synthesis of optically active functionalized tetrahydropyrans by reaction with enals using diphenylprolinol silyl ether as the organocatalyst (Scheme 16.18). The diastereoselectivity of the Michael/acetalization sequence was improved by isomerization to the thermodynamically more stable trans isomers upon basic treatment. 

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