S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis
- 15 August 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (25), 6630-6646
- https://doi.org/10.1002/chem.200600262
Abstract
In the aim of developing new procedures for efficient oligosaccharide assembly, a range of S-thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed–disarmed fashion. Moreover, the S-thiazolinyl moiety exhibited a remarkable propensity for selective activation over other common leaving groups. Conversely, a variety of leaving groups could be selectively activated over the STaz moiety, which, in turn, allowed STaz/S-ethyl and STaz/S-phenyl orthogonal approaches. To demonstrate versatility of novel STaz derivatives, a number of oligosaccharide targets have been synthesized in a convergent selective, orthogonal, and chemoselective fashion.Keywords
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