Stereoselective glycosylations using oxathiane spiroketal glycosyl donors

Novel oxathiane spiroketal donors have been synthesised and activated via an umpolung S-arylation strategy using 1,3,5-trimethoxybenzene and 1,3-dimethoxybenzene. The comparative reactivity of the resulting 2,4,6-trimethoxyphenyl (TMP)- and 2,4-dimethoxyphenyl (DMP)-oxathiane spiroketal sulfonium io...

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Bibliographic Details
Published in:Carbohydrate research 2012-02, Vol.348, p.6-13
Main Authors: Fascione, Martin A., Webb, Nicola J., Kilner, Colin A., Warriner, Stuart L., Turnbull, W. Bruce
Format: Article
Language:English
Subjects:
Anisoles - chemistry
chemical structure
Crystallography, X-Ray
Furans - chemistry
Glycosides - chemical synthesis
Glycosylation
Heterocyclic Compounds, 1-Ring - chemistry
ions
Magnetic Resonance Spectroscopy
Molecular Structure
organic compounds
Oxathiane
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemistry
Spiro Compounds - chemistry
Spiroketal
Stereoisomerism
Sulfonium Compounds - chemistry
Thioglycosides - chemical synthesis
α-Glycoside
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Summary:Novel oxathiane spiroketal donors have been synthesised and activated via an umpolung S-arylation strategy using 1,3,5-trimethoxybenzene and 1,3-dimethoxybenzene. The comparative reactivity of the resulting 2,4,6-trimethoxyphenyl (TMP)- and 2,4-dimethoxyphenyl (DMP)-oxathiane spiroketal sulfonium ions is discussed, and their α-stereoselectivity in glycosylation reactions is compared to the analogous TMP- and DMP-sulfonium ions derived from an oxathiane glycosyl donor bearing a methyl ketal group. The results show that the stereoselectivity of the oxathiane glycosyl donors is dependent on the structure of the ketal group and reactivity can be tuned by varying the substituent on the sulfonium ion.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.07.020