A Novel -Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose
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- 作者：Stefan Oscarson and Fernando W. Sehgelmeble
- 刊名：Journal of the American Chemical Society
- 出版年：2000
- 出版时间：September 20, 2000
- 年：2000
- 卷：122
- 期：37
- 页码：8869 - 8872
- 全文大小：153K
- 年卷期：v.122,no.37(September 20, 2000)
- ISSN：1520-5126
文摘
A new concept for the construction of 
-D-fructofuranosides based on the idea of locking the anomericCH2OH group to the 
-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycosidefructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridgehave been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) aspromoter. The couplings were stereospecific to give -D-fructofuranosyl disaccharides in high yields. Usingthis approach, sucrose has been synthesized stereospecifically in 80% yield.
-D-fructofuranosides based on the idea of locking the anomericCH2OH group to the -side through an internal bridge to the 4-hydroxyl group is presented. Thioglycosidefructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridgehave been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) aspromoter. The couplings were stereospecific to give -D-fructofuranosyl disaccharides in high yields. Usingthis approach, sucrose has been synthesized stereospecifically in 80% yield.