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Rotational isomerism about the C-5C-6 bond of 6-O-trityl derivatives of aldohexopyranoses, and of analogs of d-galactopyranose modified at C-4

✍ Scribed by David M. Mackie; Asafu Maradufu; Arthur S. Perlin

Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
656 KB
Volume
150
Category
Article
ISSN
0008-6215

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✦ Synopsis

Differences in rotational isomerism about the C-5-C-6 bond of 4-O-acetyl-6-0-tritylaldohexopyranose derivatives in the &co and 11u1nn0, as compared with the gulucto, series are reflected in different contributions towards diamagnetic shielding of the acetoxyl protons, and rotatory characteristics of the compounds. Among 4-deoxy-4-halogen0 analogs of methyl /3-D-galactopyranoside, rotational isomerism varies little, based on H-5,6,6' coupling, whereas the 6,6'-protons exhibit enhanced anisochronism as the mass of the halogen atom increases. The identification of resonance signals due to H-6, and H-6,, respectively, provides a basis for the consideration of these findings.

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