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Stereoselective synthesis of a fragment of mycobacterial arabinan
Authors:Ishiwata Akihiro  Akao Hiroko  Ito Yukishige
Institution:RIKEN (Institute of Physical and Chemical Research), Wako-shi, Saitama 351-0198, Japan.
Abstract:Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-(1,2-cis)-selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. Beta-selectivity was drastically enhanced by using donors protected with 3,5-TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology. reaction: see text].
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