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Convergent synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O44
Affiliation:1. Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India;2. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;1. Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata, 700054, India;2. Parasitology Laboratory, Department of Zoology (Centre for Advanced Studies), Visva-Bharati University, Santiniketan, 731235, West Bengal, India;3. Department of Biotechnology, School of Bioengineering, SRM University, Kattankulathur, 603203, Tamil Nadu, India;1. Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Americo Vespucio 49, 41092 Sevilla, Spain;2. Instituto de Química Avanzada de Cataluña, IQAC, CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Jordi Girona 18-26, E-08034 Barcelona, Spain;1. Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India;2. Bose Institute, Department of Biophysics, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India;3. Parasitology Laboratory, Department of Zoology (Centre for Advanced Studies), Visva-Bharati University, Santiniketan 731235, West Bengal, India;1. The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, PR China;2. National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China;1. Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110 007, India;2. Department of Chemistry, St. Stephen''s College, University of Delhi, Delhi, 110 007, India
Abstract:A convergent synthetic strategy has been developed for the synthesis of a pentasaccharide fragment corresponding to the O-antigen of Salmonella enterica O44 strain. An intermediate tetrasaccharide derivative was prepared by a [2+2] block glycosylation of two disaccharide derivatives. The p-methoxybenzyl (PMB) group has been used as the in situ temporary protecting group minimizing the number of functional group manipulation steps. The application of the armed–disarmed glycosylation concept reduced the number of steps in the synthetic strategy. The glycosylation steps were highly stereoselective and high yielding.
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