Synthesis and hydrogenolysis of dioxolane-type diphenylmethylene and fluoren-9-ylidene carbohydrate acetals containing a neighbouring substituted hydroxyl function

Article abstract of DOI:10.1080/07328309708005742

Series of dioxolane-type diphenylmethylene and fluoren-9-ylidene acetals of hexoses containing adjacent O-alkyl, deoxy or hydroxy functions were prepared and hydrogenolysed with the LiAlH₄-AlCl₃ reagent. The observed direction of ring-cleavage was discussed in terms of different influences, such as complex formation and orientation of the hydride reagent, the configurational arrangements of the free OH group to one of the oxygen atoms of the dioxolane ring, as well as the conformational relationship of the rings present in the 1,6-anhydro derivatives.

Full text of DOI:10.1080/07328309708005742

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Synthesis and Hydrogenolysis of
Dioxolane-Type Diphenyl-Methylene and
Fluoren-9-Ylidene Carbohydrate Acetals
Containing a Neighbouring Substituted
Hydroxyl Function
János Hajkó a , Anikó Borbás a , Gabriella Szabovik b , Mária Kajtár-
Peredy c & András Lipták a b
a Research Group for Carbohydrates of the Hungarian Academy of
Sciences , P. O. Box 55, H-4010, Debrecen, Hungary
b Department of Biochemistry , L. Kossuth University , P. O. Box 55,
H-4010, Debrecen, Hungary
c NMR Laboratory, Central Research Institute of Chemistry , P. O. Box
17, H-1525, Budapest, Hungary
Published online: 23 Aug 2006.
To cite this article: János Hajkó , Anikó Borbás , Gabriella Szabovik , Mária Kajtár-Peredy & András
Lipták (1997) Synthesis and Hydrogenolysis of Dioxolane-Type Diphenyl-Methylene and Fluoren-9-
Ylidene Carbohydrate Acetals Containing a Neighbouring Substituted Hydroxyl Function, Journal of
Carbohydrate Chemistry, 16:7, 1123-1144, DOI: 10.1080/07328309708005742
To link to this article: http://dx.doi.org/10.1080/07328309708005742
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