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Syntheses of model oligosaccharides of biological significance.Synthesis of methyl 3,6-DI-O-(α-d-mannopyranosyl)-α-d-mannopyranoside and the corresponding mannobiosides

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DOIResolve DOI: https://doi.org/10.1016/S0008-6215(82)80004-9
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FormatText, Article
Subjectassignments; carbohydrate conformation; chemical synthesis; disaccharides; glycoproteins; glycosylation; indicators and reagents; LED; Magnetic Resonance Spectroscopy; membrane proteins; spectra; yield
Abstract
Methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-α-d-mannopyranoside(12) was prepared in 90 % yield by Helferich glycosylation of methyl 2-O-allyl-4,6-O-benzylidene-α-d-mannopyranoside (9) with tetra-O-acetyl-α-d-mannopyranosyl bromide (11). Removal of the benzylidene group and second Helferich glycosylation with 11 led to methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-α-d-mannopyranoside (14) which, after deallylation and Zemplén deacetylation, gave the title compound 5. The disaccharides methyl 3-O-(α-d-mannopyranosyl)-α-d-mannopyranoside (7) and methyl 6-O-(α-d-mannopyranosyl)-α-d-mannopyranoside (6) have also been synthesized. Complete assignments of the ¹H-n.m.r. spectra of the compounds 5, 6, and 7 are given.
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  • Carbohydrate Research 103, no. 1: 15–28.
LanguageEnglish
Peer reviewedYes
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NRC numberWINNIK1982
NPARC number9377807
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Record identifier403f9c23-d7db-4ea3-aced-766c096b672f
Record created2009-07-10
Record modified2020-03-13
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