Section 32
Chapter 31,490

Formation of amphiphilic cyclodextrins via hydrophobic esterification at the secondary hydroxyl face

Zhang, P.; Ling C C.; Coleman, A.W.; Parrot Lopez, H.; Galons, H.

Tetrahedron Letters 32(24): 2769-2770


ISSN/ISBN: 0040-4039
DOI: 10.1016/0040-4039(91)85081-f
Accession: 031489499

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Esterification at the O2 and O3 positions of -cyclodextrin has been achieved in high overall yield via protection by the ButMe2Si- group at the O6 position and the use of the dimethylaminopyridine as an acylation catalyst. The silyl protecting group was removed by use of BF3·Et2O to give the novel amphiphilic -cyclodextrin derivatives. The resulting amphiphilic compounds form mixed vesicules with phospholipids.

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