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The Rearrangement Reaction of Some Acetylated Unsaturated 2-Acetamidoaldose Derivatives. Selective Removal of one N-Acetyl Group from 2-(N-acetylacetamido) Compounds

N. Pravdić ; Department of Organic Chemistry and Biochemistry, »Ruder Bo!ikovic« Institute, 41000 Zagreb, Croatia, Yugoslavia
B. Židovec ; Department of Organic Chemistry and Biochemistry, »Ruder Bo!ikovic« Institute, 41000 Zagreb, Croatia, Yugoslavia
H. G. Fletcher ; National Institute of Arthritis, Metabolism, and Digestive Diseases, National Institutes of Health, Public Health Service, U. S. Department of Health, Education, and Welfare, Bethesda, Md. 20014, U.S. A.


Puni tekst: engleski pdf 10.832 Kb

str. 333-342

preuzimanja: 230

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Sažetak

Two pairs of anomers, the l ,4,6-tri-0-acetyl-2-(N-acetylacetamido)-
2,3-dideoxy-o-hex-2-enopyranoses of the erythro- (II and III)
and the threo- series (IV and VI) have been prepared and character;
ized. The molecular conformation of these substances has been
discussed on the basis of their NMR spectral characteristics. It is
suggested that the a-anomers II and IV adopt the H~ conformation
as the favorable one, while the B-anomers III and VI most probably
tend to take a slightly modified H~ conformation.
A convenient preparative method for selective removal of one
N-acetyl group from 0-acetylated N-acetylacetamido compounds is
described. The reaction can be carried out in aqueous dioxane solution
at room temperature in the presence of an ammonium salt
at pH ca. 9.

Ključne riječi

Hrčak ID:

197029

URI

https://hrcak.srce.hr/197029

Datum izdavanja:

30.6.1973.

Posjeta: 469 *