Next Article in Journal
(22E,24S)-24-Propylcholest-5en-3α-acetate: A New Steroid from the Stembark Aglaia angustifolia (Miq.) (Meliaceae)
Next Article in Special Issue
8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity
Previous Article in Journal
Half-Sandwich Arene-Osmium(II) Complexes with Phosphinite Ligands
Previous Article in Special Issue
Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses
 
Search for Articles:
Title / Keyword
Author / Affiliation
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
Journals
Molbank
Volume 2020
Issue 1
10.3390/M1111
molbank-logo
Submit to this Journal Review for this Journal Edit a Special Issue
► Article Menu

Article Menu

Printed Edition

A printed edition of this Special Issue is available at MDPI Books....
share announcement thumb_up
...
textsms
...
Open AccessCommunication

Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block

by
Eleni Dimitriou
and
Gavin J. Miller
*
Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire ST5 5BG, UK
*
Author to whom correspondence should be addressed.
Molbank 2020, 2020(1), M1111; https://doi.org/10.3390/M1111
Received: 13 December 2019 / Revised: 14 January 2020 / Accepted: 16 January 2020 / Published: 18 January 2020
(This article belongs to the Special Issue Molecules from Side Reactions)
View Full-Text Download PDF
Browse Figure

Abstract

Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric sulfoxide products was achieved. The product was fully characterized by 1H, 13C and 2D NMR alongside MS analysis. View Full-Text
Keywords: glycosyl sulfoxide; uronate; thioglycoside oxidation; mannose glycosyl sulfoxide; uronate; thioglycoside oxidation; mannose
►▼ 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 Materials

SciFeed

Share and Cite

MDPI and ACS Style

Dimitriou, E.; Miller, G.J. Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block. Molbank 2020, 2020, M1111. https://doi.org/10.3390/M1111

AMA Style

Dimitriou E, Miller GJ. Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block. Molbank. 2020; 2020(1):M1111. https://doi.org/10.3390/M1111

Chicago/Turabian Style

Dimitriou, Eleni; Miller, Gavin J. 2020. "Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block" Molbank 2020, no. 1: M1111. https://doi.org/10.3390/M1111

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Metrics

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop