Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside

@article{Marinoalbernas1987SynthesisOA,
  title={Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-$\beta$-d-glucopyranosyl)-2,3-di-O-methyl-$\alpha$-l-rhamnopyranoside},
  author={J. R. Marino-albernas and vicente Verez-Bencomo and Leandro Gonz{\'a}lez and Carlos S. P{\'e}rez},
  journal={Carbohydrate Research},
  year={1987},
  volume={165},
  pages={197-206}
}
16 Citations
Synthesis of 3,6-di-O-methyl-β-d-glucopyranose conjugates
Abstract3,6-Di-O-methyl-β-d-glucopyranose neoglycoconjugates with bovine serum albumine and poly(acrylamide) carrier were obtained, which differ in the aglycon nature, linking pattern, and
Synthesis of a disaccharide of phenolic glycolipid from Mycobacterium leprae (PGL-I) and its conjugates with bovine serum albumin
TLDR
A terminal disaccharide fragment of phenolic glycolipid from Mycobacterium leprae (PGL-I) was synthesized as a glycoside with 4-(2-aminoethoxy)phenyl aglycon for the synthesis of a series of neoglycoconjugates with bovine serum albumin with different degrees of substitution.
Glycosides of Monoallyl Diethylene Glycol. A New Type of Spacer Group for Synthetic Oligosaccharides
Abstract The preparation of spacer-armed synthetic oligosaccharides, which can be coupled to either proteins or polymers for use respectively as immunogens or immunoadsorbants for affinity
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References

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The Allyl Group for Protection in Carbohydrate Chemistry, Part 14.1 Synthesis of 2, 3-Di-O-Methyl-4-O-(3, 6-Di-O-Methyl-β-D-Glucopyranosyl)-L-Rhamnopyranose (and its α-Propyl Glycoside): A Haptenic Portion of the Major Glycolipid from Mycobacterium Leprae
Abstract 3, 6-Di-O-methyl-d-glucose was prepared via 5-O-allyl-1, 2-O-isopropylidene-3-O-methyl-αd-glucofuranose and was converted into 2, 4-di-O-acetyl-3, 6-di-o-methyl-dD-glucopyranosy 1 chloride.
Use of an artificial antigen containing the 3,6-di-O-methyl-beta-D-glucopyranosyl epitope for the serodiagnosis of leprosy.
TLDR
3,6-di-O-methyl-beta-D-glucopyranose in its cyclic hemiacetal form is necessary for binding anti-glycolipid IgM from leprosy patients and the prospects of a fully synthetic specific antigen for the worldwide serodiagnosis of lepropsy look promising.
Chemical synthesis and serology of disaccharides and trisaccharides of phenolic glycolipid antigens from the leprosy bacillus and preparation of a disaccharide protein conjugate for serodiagnosis of leprosy
TLDR
The 3,6-di-O-methyl-beta-D-glucopyranosyl substituent was recognized as the primary antigen determinant in phenolic glycolipid I and shown to be highly active in the serodiagnosis of leprosy.
A novel phenolic glycolipid from Mycobacterium leprae possibly involved in immunogenicity and pathogenicity
TLDR
Surprisingly large quantities of the glycolipid were also found in infected liver residue freed of M. leprae, suggesting that it may be responsible for the electron-transparent "foam" surrounding the organism in infected lepromatous tissue.
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