Multigram-scale synthesis of an orthogonally protected 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT) building block

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• 作者：A.E. Christina ; V.M. Blas Ferrando ; F. de Bordes ; W.A. Spruit ; H.S. Overkleeft ; J.D.C. Codé ; e ; ^{jcodee@chem.leidenuniv.nl} ; G.A. van der Marel ; ^{marel_g@chem.leidenuniv.nl}
• 关键词：Deoxysugar ; Intramolecular substitution ; Zwitterionic polysaccharide
• 刊名：Carbohydrate Research
• 出版年：2012
• 期刊代码：15_00086215
• 类别：ch
• 出版时间：15 July, 2012
• 卷：356
• 期：Complete
• 页码：282-287
• 文件大小：284 K

摘要

Reported is the gram-scale synthesis of tert-butyldiphenylsilyl 4-(N-benzyloxycarbonyl)-amino-2-azido-2,4,6-trideoxy-尾-d-galactopyranoside, which represents an orthogonally protected 2,4-diamino-d-fucose building block, a common constituent of various zwitterionic polysaccharides. The building block has been synthesized from d-glucosamine in 19%overall yield over 14 steps, requiring 5 chromatographic purifications. The key step in the synthesis is the introduction of the C-4 amino substituent, which has been accomplished by a one-pot three step procedure, involving regioselective C-3-O-trichloroacetimidate formation, C-4-O-triflation, and intramolecular substitution. The building block can be used as an acceptor and is readily transformed into a donor glycoside.