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Synthesis of rigid multivalent scaffolds based on adamantane.

ABSTRACT: An efficient route to novel 1,3,5,7-tetrasubstituted derivatives of adamantane is described. This route starts from adamantane and gives the tetrafunctionalized derivative 9 in eight steps with an overall yield of 23%. These tetrahedrally shaped molecules possess three identical arms terminated by an activated carboxylic acid derivative and a protected amino function in the 1-position. We propose these tetravalent cage compounds such as 9 as scaffolds for the assembly of ligand/marker conjugates for studies of multivalent ligand receptor interactions. [reaction: see text]

SUBMITTER: Maison W

PROVIDER: S-EPMC1421509 | biostudies-literature | 2004 Nov

REPOSITORIES: biostudies-literature

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Synthesis of rigid multivalent scaffolds based on adamantane.

Maison Wolfgang W Frangioni John V JV Pannier Nadine N

Organic letters 20041101 24

An efficient route to novel 1,3,5,7-tetrasubstituted derivatives of adamantane is described. This route starts from adamantane and gives the tetrafunctionalized derivative 9 in eight steps with an overall yield of 23%. These tetrahedrally shaped molecules possess three identical arms terminated by an activated carboxylic acid derivative and a protected amino function in the 1-position. We propose these tetravalent cage compounds such as 9 as scaffolds for the assembly of ligand/marker conjugates ...[more]

PMID: 15548077

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