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A fluorous phosphate protecting group with applications to carbohydrate synthesis.

ABSTRACT: 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.

SUBMITTER: Liu L

PROVIDER: S-EPMC3127408 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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A fluorous phosphate protecting group with applications to carbohydrate synthesis.

Liu Lin L Pohl Nicola L B NL

Organic letters 20110308 7

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. ...[more]

PMID: 21384825

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