Synthesis of sugar oxime ether surfactants

The first sugar oxime ether surfactants (SOESurfs) are reported. A straightforward synthesis of a novel class of sugar surfactants is described. The key step is the chemoselective condensation of a hydrophobic alkoxyamine with the resident aldehyde/ketone moiety on a hydrophilic sugar. Neither prote...

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Bibliographic Details
Published in:Tetrahedron letters 2014-08, Vol.55 (35), p.4962-4965
Main Authors: Ewan, Harrison S., Muli, Christine S., Touba, Steven, Bellinghiere, Amy T., Veitschegger, Anne M., Smith, Travis B., Pistel, William L., Jewell, William T., Rowe, Rebecca K., Hagen, John P., Palandoken, Hasan
Format: Article
Language:English
Subjects:
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Alkoxyamine
Aminooxy
Ethers
Ketones
Oxime ether
Oximes
Purification
Sugar oxime ether surfactant
Sugars
Surfactants
Synthesis (chemistry)
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Summary:The first sugar oxime ether surfactants (SOESurfs) are reported. A straightforward synthesis of a novel class of sugar surfactants is described. The key step is the chemoselective condensation of a hydrophobic alkoxyamine with the resident aldehyde/ketone moiety on a hydrophilic sugar. Neither protection/deprotection of the sugars nor extensive product purification is required. The method allows for the facile adjustment of hydrophobic and hydrophilic domains of the sugar oxime ether surfactant and uses inexpensive, readily accessible, and renewable materials.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.07.036