616238-31-4Relevant academic research and scientific papers
Synthesis of Mannosidase-Stable Man3and Man4Glycans Containing S-linked Manα1→2Man Termini
Neralkar, Mahesh,Tian, Leiming,Redman, Richard L.,Krauss, Isaac J.
supporting information, p. 3053 - 3057 (2021/05/05)
Oligomannose glycans are of interest as HIV vaccine components, but they are subject to mannosidase degradation in vivo. Herein, we report the synthesis of oligosaccharides containing a thio linkage at the nonreducing end. A thio-linked dimannose donor participates in highly stereoselective glycosylations to afford trimannose and tetramannose fragments. Saturation transfer difference nuclear magnetic resonance (STD NMR) studies show that these glycans are recognized by HIV antibody 2G12, and we confirm that the reducing terminal S-linkage confers complete stability against x. manihotis mannosidase.
A building block approach to the synthesis of a family of S-linked α-1,6-oligomannosides
Belz, Tyson,Williams, Spencer J.
, p. 38 - 47 (2016/07/06)
The syntheses of α-1,6-S-linked methyl di-, tetra- and hexamannosides are reported. The sulfur linkages are generated through coupling of thiolates (derived from anomeric thioacetates or isothiouronium bromides) with 6-deoxy-6-iodo sugars. Two approaches are detailed that involve [2 + 2 + 2] construction from either the reducing end or the non-reducing end. In constructing from the reducing end, coupling of a disaccharide thioacetate with a 6'-iodo reducing end disaccharide, followed by activation of the resulting tetrasaccharide to a 6'''-iodide, and iterative coupling with the same disaccharide thioacetate afforded the S-linked hexasaccharide, as well as the intermediate di- and tetrasaccharides. On the other hand, construction from the non-reducing end involved coupling of the above disaccharide thioacetate with an anomeric S-trityl protected 6'-iodo disaccharide. The resulting S-trityl tetrasaccharide was converted to a tetrasaccharide thioacetate, which was coupled with the same anomeric S-trityl protected 6'-iodo disaccharide to afford the hexasaccharide, which was elaborated to the methyl thioglycoside. The developed methodology may prove useful for the construction of other S-linked oligosaccharides.
2-Haloethyl 1-thioglycosides as new tools in glycoside syntheses. Part 1: Preparation, characteristics, general reactions
Krueger, Andreas,Pyplo-Schnieders, Jutta,Redlich, Hartmut,Winkelmann, Paer
, p. 1843 - 1876 (2007/10/03)
2-Haloethyl 1-thioglycosides are excellent leaving groups when the 2-haloethyl function is activated with silver salts or Lewis acids. These thioglycosides can be synthesized on the original Cerny route or for better compatibility with the needs of a more complex glycoside synthesis, in stepwise procedures via 2-(2-tetrahydropyran-2-yloxy)ethyl glycosides or trityl 1-thioglycosides. The initial step in glycosidation reaction presumably proceeds via a thiiranium ion, which is responsible for their increased reactivity compared with normal thioethers as leaving groups in glycoside syntheses. Basic features of this new system with respect to reactivity and selectivity in disaccharide syntheses are described.
A general method for the synthesis of sugar 2-C-sulfonic acids by 1 → 2 arylthio group migration in acid-sensitive thioglycosides. Direct transformation of thiotrityl ethers into C-sulfonic acids
Liptak, Andras,Sajtos, Ferenc,Janossy, Lorant,Gehle, Diethmar,Szilagyi, Laszlo
, p. 3671 - 3674 (2007/10/03)
(Matrix presented) Fully protected triphenylmethyl 2-O-mesyl-1-thio-β- D-gluco- (14) and -α-D-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 → 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-α-D-manno- (15) and -β-D
