4.8 Article

A Fluorous Phosphate Protecting Group with Applications to Carbohydrate Synthesis

Journal

ORGANIC LETTERS
Volume 13, Issue 7, Pages 1824-1827

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol2003435

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Funding

  1. National Institutes of Health [1R01GM090280]
  2. Direct For Mathematical & Physical Scien
  3. Division Of Chemistry [0840434, 0946687] Funding Source: National Science Foundation

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The first fluorous protecting group for phosphate is reported. This group can be used as a facile tag for purification and be removed under mild reducing conditions using zinc and ammonium formate. Synthesis of a disaccharide from leishmania using this fluorous protecting group demonstrated the group's stability to the acidic conditions necessary for glycosylation as well as its orthogonality to several other common protecting groups.

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