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

Download
  1. Get@NRC: Syntheses of model oligosaccharides of biological significance.Synthesis of methyl 3,6-DI-O-(α-d-mannopyranosyl)-α-d-mannopyranoside and the corresponding mannobiosides (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1016/S0008-6215(82)80004-9
AuthorSearch for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleCarbohydrate Research
Volume103
Issue1
Pages1528; # of pages: 14
Subjectassignments; carbohydrate conformation; chemical synthesis; disaccharides; glycoproteins; glycosylation; indicators and reagents; LED; Magnetic Resonance Spectroscopy; membrane proteins; spectra; yield
AbstractMethyl 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.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada
Peer reviewedYes
NRC publication
This is a non-NRC publication

"Non-NRC publications" are publications authored by NRC employees prior to their employment by NRC.

NRC numberWINNIK1982
NPARC number9377807
Export citationExport as RIS
Report a correctionReport a correction
Record identifier403f9c23-d7db-4ea3-aced-766c096b672f
Record created2009-07-10
Record modified2016-08-31
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)