Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone
by
Michael R. Imrich
and Thomas Ziegler *
Michael R. Imrich and Thomas Ziegler *
Institute of Organic Chemistry, University of Tuebingen, Auf der Morgenstelle 18, 72076 Tuebingen, Germany
*
Author to whom correspondence should be addressed.
Molbank 2019, 2019(4), M1096; https://doi.org/10.3390/M1096
Received: 18 November 2019 / Revised: 2 December 2019 / Accepted: 4 December 2019 / Published: 10 December 2019
(This article belongs to the Special Issue Molecules from Side Reactions)
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l-psicose derivative as an anomeric mixture in 72% yield. Both methylated psicoses were further converted into 1,2-O-isopropylidene-3,4,6-tri-O-methyl-d- and l-psicofuranosides, the respective α- and β-anomers of which could be separated and characterized.
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Keywords:
ribose; psicose; ketose; rare sugar; hydroxy methylation
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MDPI and ACS Style
Imrich, M.R.; Ziegler, T. Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone. Molbank 2019, 2019, M1096.
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