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
Open AccessCommunication

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

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)
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

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 Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop