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Profiling sulfonate ester stability: identification of complementary protecting groups for sulfonates.

ABSTRACT: Sulfonation is prized for its ability to impart water-solubility to hydrophobic molecules such as dyes. This modification is usually performed as a final step, since sulfonated molecules are poorly soluble in most organic solvents, which complicates their synthesis and purification. This work compares the intrinsic lability of different sulfonate esters, identifying new sulfonate protecting groups and mild, selective cleavage conditions.

SUBMITTER: Miller SC

PROVIDER: S-EPMC3225188 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Profiling sulfonate ester stability: identification of complementary protecting groups for sulfonates.

Miller Stephen C SC

The Journal of organic chemistry 20100701 13

Sulfonation is prized for its ability to impart water-solubility to hydrophobic molecules such as dyes. This modification is usually performed as a final step, since sulfonated molecules are poorly soluble in most organic solvents, which complicates their synthesis and purification. This work compares the intrinsic lability of different sulfonate esters, identifying new sulfonate protecting groups and mild, selective cleavage conditions. ...[more]

PMID: 20515067

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