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Preparation of α and β anomers of various isomeric methyl O-D-galactopyranosyl-D-galactopyranosides. Standards for interpretation of ¹³C-n.m.r. spectra of D-galactopyranans

DOIResolve DOI: https://doi.org/10.1016/S0008-6215(00)80790-9
AuthorSearch for: 1
Affiliation
  1. National Research Council of Canada. Prairie Regional Laboratory
FormatText, Article
Abstract
The four isomers of methyl O-β-d-galactopyranosyl-β-D-galactopyranoside were prepared by condensation of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide with appropriate, partially O-substituted derivatives of methyl β-D-galactopyranoside. Reaction of 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose with the same acceptors, in the presence of mercuric bromide, led to the formation of α and β linkages. Thus, it was possible to assign ¹³C-n.m.r. resonances of α and β anomers of methyl O-D-galactopyranosyl-β-D-galactopyranosides. In terms of application of these shift values and those of related D-galactobioses to the structural analysis of D-galactopyranans by shift comparisons, some generalizations can be made. For β-D-galactopyranans, the resonances of glycosyloxylated carbon atoms of methyl O-β-D-galactopyranosyl-β-D-galactopyranosides are sensitive to structure and appear to have typical values, whereas limited variation was observed with shifts of C-1′ signals. On the other hand, for assigning structures to D-galactopyranans containing α linkages, the C-1′ shifts (at higher field) of methyl O-α-D-galactopyranosyl-β-D-galactopyranosides are sensitive to linkage position, whereas those of glycosyloxylated carbon atoms vary only a little.
Publication date
PublisherElsevier
In
  • Carbohydrate Research 101, no. 1 (February 1982): 13–20.
LanguageEnglish
Peer reviewedYes
IdentifierS0008621500807909
NRCC-19717
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Record identifier073e86a6-fb56-4428-91c1-17ca4c8eae97
Record created2023-11-16
Record modified2023-11-16

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