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![The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F54498.jpg&w=3840&q=50)
The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
Published on: November 28, 2016
Divergent Synthesis of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Glycosides Containing α-(2→4)-Linked Kdo-Kdo Unit
Xian-Yang Zhou1, Pan Yang1, Sheng Luo1
1Key Laboratory of Drug-Targeting and Drug Delivery Systems of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drugs and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041, P. R. China.
Abstract:
A convenient and divergent approach was developed to prepare diverse bacterial 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) oligosaccharides containing a Kdo-α-(2→4)-Kdo fragment. The orthogonal protected α-(2→4) linked Kdo-Kdo disaccharide 3, serving as a common precursor, was divergently transformed into the corresponding 8-, 8'-, and 4'-hydroxy disaccharides 5, 7, and 14, respectively. Then, these alcohols were glycosylated, respectively, with the 5,7-O-di-tert-butylsilylene (DTBS) protected Kdo thioglycoside donors 1 or 2 in an α-stereoselective and high-yielding manner to afford a range of Kdo oligosaccharides. Finally, removal of all protecting groups of the newly formed glycosides resulted in the desired free Kdo oligomer.
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