Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a d-xylose moiety as a protecting group |
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| Institution: | 1. Department of Chemistry, University of Hull, Hull HU6 7RX, UK;2. Laboratoire des Glucides, Université de Picardie, F-80039 Amiens, France;1. Sierra Epigenetics LLC, Granite Bay, CA;2. Department of Pathology, Windsor University, Cayon, St Kitts;3. Department of Microbiology and Immunology, Pennsylvania State University College of Medicine and Penn State Hershey Cancer Institute, Hershey, PA;4. Department of Medicine/Hematology–Oncology, UVA Cancer Center, Charlottesville, VA;1. Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India;2. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India;3. Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India |
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| Abstract: | 1,2-O-Isopropylidene-α-d-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzoc]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. |
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