preparation and crystal structure of (1s, 5s, 7s, 8r)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one准备和晶体结构(1 s,5 s,7,8 r)8-hydroxy-7-phenyl-2,6-dioxabicyclo 3.3.0 octan-3-one.pdfVIP

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preparation and crystal structure of (1s, 5s, 7s, 8r)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one准备和晶体结构(1 s,5 s,7,8 r)8-hydroxy-7-phenyl-2,6-dioxabicyclo 3.3.0 octan-3-one.pdf

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preparation and crystal structure of (1s, 5s, 7s, 8r)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one准备和晶体结构(1 s,5 s,7,8 r)8-hydroxy-7-phenyl-2,6-dioxabicyclo 3.3.0 octan-3-one

Molecules 2003, 8, 599-606 molecules ISSN 1420-3049 Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy- 7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one Vratislav Langer 1,*, Dalma Gyepesová 2, Marian Koman 3, Peter Kapitán 4, Matej Babjak 4, Tibor Gracza 4 and Miroslav Koóš 5 1 Department of Environmental Inorganic Chemistry, Chalmers University of Technology, SE-41296 Gˆteborg, Sweden 2 Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-84536 Bratislava, Slovakia 3 Department of Inorganic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia 4 Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia 5 Institute of Chemistry, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia * Author to whom correspondence should be addressed. E-mail: langer@inoc.chalmers.se; Fax: (+46)- 31-7722846; Tel.: (+46)-31-7722877 Received: 4 September 2002; in revised form: 25 June 2003 / Accepted: 28 June 2003 / Published: 15 July 2003 Abstract: The absolute configuration at two newly formed stereogenic centres (5S, 7S) during the key steps of the total synthesis of naturally occuring goniothalesdiol was established by single-crystal X-ray diffraction analysis relative to stereocentres (1S, 8R) of the title compound (alternatively named 3,6-anhydro-2-deoxy-6-phenyl-L-ido-1,4- hexonolactone, C H O ). The conformation of both 5-membered lactone and furanose 12 12 4 fused