Two Straightforward Strategies for the Synthesis of Thiodisaccharides with a Furanose Unit as the Nonreducing End

Repetto, Evangelina; Marino, Carla; Uhrig, Marı́a Laura; Varela, Oscar

doi:10.1002/ejoc.200700874

Cited by 26 publications

(22 citation statements)

References 29 publications

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“…17 In another approach, the Michael addition of thioaldoses to the α,β-unsaturated systems of sugar enones, successfully produced 3-and 4-deoxythiodisaccharides and other structurally related compounds. [18][19][20][21][22][23][24] Some of the disaccharides obtained proved to be good inhibitors of glycosidases such as the E. coli β-galactosidase 21,24 and others. 25 The ring-opening reaction of epoxides also yielded (13) and (14) thiodisaccharides under stereoselective processes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate

2019

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The syntheses of β-S-GlcA(13)GlcNAc and β-S-Gal(13)GlcNAc thiodisaccharides were achieved by SN2 displacement of a triflate group allocated at 3-position of a convenient 2-azido-4,6-O-benzylidene-2-deoxy-β-D-allopyranose precursor, by the corresponding nucleophilic suitable protected thioaldoses derived from GlcA and Gal.The study of the reaction led to the finding that the vinylazide formed by the competitive E2 reaction of the mentioned triflate, was an interesting precursor of a new kind of 2,3dideoxy-2-azido-(12) thiodisaccharides, through an addition reaction. The determination of the stereochemistry of the new stereocenter at C-2 was achieved by NOESY experiments. Final protecting group manipulation of the (13) thiodisaccharides led to a family of derivatives that could be used as building blocks for the synthesis of more complex glycomimetics.

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Section: Introductionmentioning

confidence: 99%

Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate

2019

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“…[1] They are particularly useful probes for enzyme inhibition studies. [3][4][5][6][7] The molecular basis of the inhibition of the β-galactosidase from E. coli by selected S-disaccharides has been studied by using a combination of NMR spectroscopy and molecular modelling techniques. [2] In our laboratory, we have synthesized a number of thiodisaccharides that proved to be inhibitors of specific glycosidases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thiodisaccharide Sulfoxides and Sulfones – Determination of the Configuration of the Sulfur Stereocentre

2013

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The oxidation of per‐O‐acetyl S‐(1→3)‐ and S‐(1→4)‐linked thiodisaccharides containing glucose, gulose and galactose residues with an excess of m‐chloroperbenzoic acid gave the corresponding sulfoxides or sulfones. Sulfones were formed when the oxidation reaction was left for longer times. The sulfoxides were obtained as diastereomeric mixtures due to the chirality of the sulfur atom. Both diastereoisomers of the S‐(1→3)‐linked thiodisaccharide sulfoxides were isolated by column chromatography, whereas the S‐(1→4)‐linked analogues could not be separated. The absolute configuration of the sulfur stereocentre of the sulfoxides was assigned using NMR spectroscopy, taking into account the preferred conformations of the molecules, and the shielding/deshielding of proton signals caused by the anisotropy of the S=O bond and related effects. Most of the thiodisaccharide sulfoxides were successfully O‐deacetylated with MeOH/Et3N/H2O, but the sulfones underwent elimination reactions under these conditions. Therefore, the oxidation was performed on unprotected thiodisaccharides, and the corresponding sulfones were obtained in very good yields.

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“…In 2008, Varela and co-workers described the use of MoO 2 Cl 2 to promote the thioglycosylation of the thiol group of 6-thiosugars by per-O-acylfuranose yielding a thiodisaccharide with complete 1,2-trans diastereocontrol (Scheme 30). 71 Chen and co-workers have also shown that MoO 2 Cl 2 shows remarkable catalytic activity for the deacylation of esters in methanol. Highly chemoselective processes were achieved for functionalized substrates possessing different ester or ether groups (Scheme 31).…”

Section: Amphoteric Lewis Acid-lewis Base Catalyzed Reactionsmentioning

confidence: 97%

Dichlorodioxomolybdenum(VI) Complexes: Useful and Readily Available Catalysts in Organic Synthesis

Hernández-Ruiz

Sanz²

2018

Synthesis

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Molybdenum(VI) dichloride dioxide (MoO2Cl2), and its addition complexes [MoO2Cl2(L)n; L = neutral ligand], are commercially or easily available and inexpensive transition-metal complexes based on a non-noble metal that can be applied as catalysts for various organic transformations. This short review aims to present the most significant breakthroughs in this field.1 Introduction2 Preparation and Reactivity of MoO2Cl2(L)n Complexes2.1 Synthesis and Structure2.2 Reactivity of Dichlorodioxomolybdenum(VI) Complexes3 Redox Processes Catalyzed by MoO2Cl2(L)n Complexes3.1 Deoxygenation Reactions Using Phosphorus Compounds3.2 Deoxygenation and Hydrosilylation Reactions Using Silanes3.3 Reduction Reactions Using Hydrogen3.4 Deoxygenation Reactions with Boranes and Thiols3.5 Reduction Reactions with Glycols3.6 Oxidation Reactions4 Ambiphilic Reactivity of MoO2Cl2 4.1 Amphoteric Lewis Acid–Lewis Base Catalyzed Reactions4.2 Lewis Acid Type Catalyzed Reactions5 Conclusion and Perspective

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Two Straightforward Strategies for the Synthesis of Thiodisaccharides with a Furanose Unit as the Nonreducing End

Cited by 26 publications

References 29 publications

Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate

Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate

Synthesis of Thiodisaccharide Sulfoxides and Sulfones – Determination of the Configuration of the Sulfur Stereocentre

Dichlorodioxomolybdenum(VI) Complexes: Useful and Readily Available Catalysts in Organic Synthesis

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