Title of article :
Stereoselective glycosylations using oxathiane spiroketal glycosyl donors Original Research Article
Author/Authors :
Martin A. Fascione، نويسنده , , Nicola J. Webb، نويسنده , , Colin A. Kilner، نويسنده , , Stuart L. Warriner، نويسنده , , W. Bruce Turnbull، نويسنده ,
Issue Information :
دوهفته نامه با شماره پیاپی سال 2012
Pages :
8
From page :
6
To page :
13
Abstract :
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.
Keywords :
Glycosylation , Spiroketal , ?-Glycoside , Oxathiane
Journal title :
Carbohydrate Research
Serial Year :
2012
Journal title :
Carbohydrate Research
Record number :
967443
Link To Document :
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