Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

Polymer-supported tin carbohydrate chemistry

D M Whitfield1, T Ogawa

  • 1National Research Council, Ottawa, Ontario, Canada.

Glycoconjugate Journal
|April 8, 1998
PubMed
Summary
This summary is machine-generated.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Chemoenzymatic iterative synthesis of difficult linkages of oligosaccharides on soluble polymeric supports.

Organic letters·2001
Same author

The conformational origin of the barrier to the formation of neighboring group assistance in glycosylation reactions: a dynamical density functional theory study.

Journal of the American Chemical Society·2001
Same author

Immunostimulant oxidized beta-glucan conjugates.

International immunopharmacology·2001
Same author

Ready access to sialylated oligosaccharide donors.

Organic letters·2001
Same author

Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison.

Carbohydrate research·2000
Same author

Synthesis of a disialylated hexasaccharide of type VIII group B Streptococcus capsular polysaccharide.

Carbohydrate research·1999

Polymer-supported tin reagents enable easier purification of carbohydrates. This method achieved regioselective acylation of methyl alpha-D-mannopyranoside, improving yields with a 5% cross-linked resin.

Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Carbohydrate Chemistry

Background:

  • Traditional tin-mediated carbohydrate modifications involve toxic reagents and complex purification.
  • Immobilizing tin reagents on a polymer support offers a potential solution for simplified product isolation and reagent recovery.

Purpose of the Study:

  • To develop a polymer-supported stannylation method for regioselective carbohydrate acylation.
  • To evaluate the efficiency and yield of this novel approach for carbohydrate derivatization.

Main Methods:

  • An alkene linker (3-buten-1-ol) was attached to chloromethylated polystyrene.
  • Photochemical hydrostannylation with dibutyltin chlorohydride created a polymer-bound tin species.
  • Hydrolysis of the polymer-bound tin chloride yielded a resin with terminal Sn-O bonds for acylation reactions.

Related Experiment Videos

Main Results:

  • Regioselective 3-O-benzoylation of methyl alpha-D-mannopyranoside was achieved, with minor amounts of other products.
  • Selective 2-O-benzoylation of methyl alpha-D-glucopyranoside resulted in a more complex mixture.
  • Initial yields were low (10-30%), but improved to approximately 60% using a 5% cross-linked resin.

Conclusions:

  • Polymer-supported tin reagents provide a viable method for simplifying the purification of acylated carbohydrates.
  • The regioselectivity and yield of the acylation are influenced by the choice of carbohydrate and the cross-linking degree of the resin.
  • Further optimization of polymer-supported stannylation could enhance its utility in carbohydrate chemistry.