Original scientific paper

3,4,6-Tri-O-acetyl-2-(N-acetylacetamido )-1,2-dideoxy-o-Iyxohex- 1-enopyranose, an Acetamido-n-galactal Derivative, and the Mechanism of its Formation from 2-Acetamido-2-deoxy-D-galactose

N. Pravdić ; Department of Organic Chemistry and Biochemistry, »Ruder Bo§kovic« Institute, · Zagreb,-Yugoslavia
H. G. Fletcher, Jr. ; National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Public Health Service, U.S. Department of Health, Education, and Welfare, Bethesda, Maryland 20014, U.S. A.

Abstract

The structure of an unsaturated amino sugar derivative, formed
in low yield when 2-acetamido-2-deoxy-o-galactose _is treated with
boiling isopropenyl acetate containing a trace of p-toluenesulfonic
acid, and formulated as 1,4,6-tri-0-acetyl-2-(N-acetylacetamido)-
2,3-dideoxy-o-threo-hex-2-enopyranose(II) in an earlier publication,
has been re-examined. Through a series of steps, including
catalytic hydrogenation, the substance has been converted into a
compound with an NMR spectrum which shows it to be 3,4,6-tri-
0-acetyl-2-(N -acetylbenzamido )-1,5-anhydro-2-deoxy-o-tali tol (X).
This fact, together with a re-examination of its NMR spectrum,
show the unsaturated compound to be 3,4,6-tri-0-acetyl-2-(N··
-acetylacetamido)-1,2-dideoxy-o-lyxo-hex-l-enopyranose (III), a
derivative of 2-acetamido-o-galactal (VI). The yield of III from
2-acetamido-2-deoxy-o-galactose has been substantially improved
through isolation of . 2-acetamido-1,3,4 , 6-tetra-0-acetyl-2-deoxy-~-
o-galactopyranose (XIII) as an intermediate and III has been
obtained in crystalline form. Evidence for the mechanism of its
formation is presented.

Keywords

Hrčak ID:

207947

URI

https://hrcak.srce.hr/207947

Publication date:

1.10.1969.

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