Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone
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.
View Full-Text
Keywords:
ribose; psicose; ketose; rare sugar; hydroxy methylation
▼
Show Figures
Graphical abstract
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
- Supplementary File 1:
PDF-Document (PDF, 6355 KiB)
- Supplementary File 2:
INCHI-Document (INCHI, 7 KiB)
- Supplementary File 3:
MOL-Document (MOL, 27 KiB)
Display in JSmol Viewer
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.
AMA Style
Imrich MR, Ziegler T. Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone. Molbank. 2019; 2019(4):M1096.
Chicago/Turabian StyleImrich, Michael R.; Ziegler, Thomas. 2019. "Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone" Molbank 2019, no. 4: M1096.
Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.
Search more from Scilit
