期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 12, 期 25, 页码 6630-6646出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600262
关键词
carbohydrates; glycosyl donors; glycosylation; synthetic methods; thioimidates
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. More-over, 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/Sphenyl 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.
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