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Monday, August 24 • 2:40pm - 3:20pm
[0199] Total Synthesis of Periploside A, a unique Pregnane Hexasaccharide with Potent Immunosuppressive Effects

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Periploside A is a pregnane hexasaccharide identified from the Chinese medicinal plant Periploca sepium, which features a unique seven-membered formyl acetal bridged orthoester (FABO) motif and shows potent immunosuppressive activities. The total synthesis of this natural product is achieved in a total of 76 steps with the longest linear sequence of 29 steps and 9.2% overall yield.[1] The FABO motif is constructed via a combination of Sinaÿ’s and Crich’s protocol for the formation of orthoester and acetal glycosides, respectively. The 2-deoxy-b-glycosidic linkages are assembled stereoselectively with judicious choice of the glycosylation methods.[2,3] The epimer at the spiro-quaternary carbon in the FABO motif has also been elaborated in a stereo-controlled manner. This epimer, as well as the synthetic analogs bearing FABO motif, retain largely the inhibitory activities of periploside A against the proliferation of T-lymphocyte, indicating the importance of the chemical connection of the FABO motif to their immunosuppressive activities.

Invited Lecturers
avatar for Biao Yu

Biao Yu

Professor, Shanghai Institute of Organic Chemistry
Shanghai Institute of Organic Chemistry, Chinese Academy of fellow  | PI, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS) , director of the State Key Laboratory of Organic Chemistry, Director, State Key Laboratory of Bioorganic and Natural Products... Read More →

Monday August 24, 2015 2:40pm - 3:20pm
Corwin East