Stereoselective synthesis of a fragment of mycobacterial arabinan |
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Authors: | Ishiwata Akihiro Akao Hiroko Ito Yukishige |
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Institution: | RIKEN (Institute of Physical and Chemical Research), Wako-shi, Saitama 351-0198, Japan. |
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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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