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Synthetic studies toward the preparation of (4R,5R)-(−)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-cyclopenten-2-one: an important synthetic intermediate for carbanucleosides
Affiliation:1. Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Buenos Aires, Argentina;2. BioLab, Instituto Universitario de Bio-Orgánica “Antonio González” (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, 38206 La Laguna, Spain;3. CONICET – Universidad de Buenos Aires, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Buenos Aires, Argentina;1. University of Łódź, Faculty of Chemistry, Department of Organic and Applied Chemistry, Tamka 12, PL-91-403 Łódź, Poland;2. University of Zurich, Department of Chemistry, Winterthurerstrasse 190, CH‐8057 Zurich, Switzerland;1. Discovery Chemistry, Merck Research Laboratories, 2000 Galloping Hill Road, Kenilworth, NJ 07033, USA;2. Pharmaron Beijing Co., Ltd, 6 Tai-He Road, BDA, Beijing 100176, China;3. Discovery Biology, Merck Research Laboratories, 770 Sumneytown Pike, West Point, PA 19486, USA
Abstract:The carbocyclic compound (4R,5R)-(−)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone 1 is an important synthetic intermediate to access a variety of carbanucleosides. Herein, synthetic studies that lead to this valuable compound employing inexpensive d-ribose as the chiral source are presented.
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