Protective group-free synthesis of 3,4-dihydroxytetrahydrofurans from carbohydrates: formal total synthesis of sphydrofuran

Kalkeren, Henri A. van; Rootselaar, Stefan van; Haasjes, Frank S.; Rutjes, Floris P. J. T.; Delft, Floris L. van

doi:10.1016/j.carres.2012.09.004

Cited by 11 publications

(7 citation statements)

References 43 publications

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“…C 5 sugars react similarly with B(C 6 F 5 ) 3 , and pretreatment provides tetrahydrofurans. 12 Addition of Et 3 SiH to these solutions led to preferential S N 2′ reduction of the allylic silyl ether (∼75:25; entries 5−7, Table 1). Reducing the temperature and adding B(C 6 F 5 ) 3 and Et 3 SiH together to 7 improved the S N 2′ selectivity to 91:9 for syn-triol 13, though the role of precyclization is not clear in this case (entry 7).…”

mentioning

confidence: 99%

Delineating The Multiple Roles of B(C₆F₅)₃ in the Chemoselective Deoxygenation of Unsaturated Polyols

2016

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confidence: 99%

Delineating The Multiple Roles of B(C₆F₅)₃ in the Chemoselective Deoxygenation of Unsaturated Polyols

2016

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“…Wittig-and HWE-type reactions have also been applieda t the reducing ends of unprotectedaldoses to providet he corre-sponding polyhydroxyalkyl olefinic derivatives. [221] However,t o the best of our knowledge,s uch methodologies did not afford glycosides and thus are outside the scope of this review.…”

Section: Horner-wadsworth-emmons Reactionmentioning

confidence: 97%

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

et al. 2017

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Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its "omics", glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

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Section: Reacting Unprotected Carbohydrates As Aldehydesmentioning

confidence: 99%

“…8a Recently, Wittig olefination of unprotected monosaccharides was utilized as a key step in the formal total synthesis of sphydrofuran. 9 A modified Wittig procedure, the Horner-Wadsworth-Emmons reaction, has likewise been applied to unprotected carbohydrates giving access to C-glycosides optimally under solvent-free conditions. 10 Scheme 2 Synthesis of polyhydroxylated lactone by Wittig reactionhydrogenation sequence from unprotected D-mannose Tin-mediated allylation of unprotected carbohydrates as a method to extend the carbon chain by three carbon atoms was exploited for the first time in 1991 by Schmid and Whitesides.…”

Section: Reacting Unprotected Carbohydrates As Aldehydesmentioning

confidence: 99%

Unprotected Carbohydrates as Starting Material in Chemical Synthesis: Not Just a Challenge but an Opportunity

Saloranta

Leino

2015

Synlett

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Development of reaction sequences that utilize renewable resources, such as carbohydrates, as starting material is of topical interest. Particularly attractive are reaction protocols where unprotected mono-and oligosaccharides are applied. Herein, selected approaches for direct derivatization of unprotected carbohydrates are highlighted. Ultimately, such methodologies are also applicable for natural polysaccharides resulting in rapid development of novel functional biobased materials for future applications. 1 Introduction 2 Reacting Unprotected Carbohydrates as Aldehydes 3 Approaches for Selective Reactions Targeting the Nonanomeric Hydroxyl Groups on Unprotected Carbohydrates 4 Protecting-Group-Free Synthesis of Glycoclusters and Glycoconjugates 5 Conclusions

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Protective group-free synthesis of 3,4-dihydroxytetrahydrofurans from carbohydrates: formal total synthesis of sphydrofuran

Cited by 11 publications

References 43 publications

Delineating The Multiple Roles of B(C₆F₅)₃ in the Chemoselective Deoxygenation of Unsaturated Polyols

Delineating The Multiple Roles of B(C₆F₅)₃ in the Chemoselective Deoxygenation of Unsaturated Polyols

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Unprotected Carbohydrates as Starting Material in Chemical Synthesis: Not Just a Challenge but an Opportunity

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Protective group-free synthesis of 3,4-dihydroxytetrahydrofurans from carbohydrates: formal total synthesis of sphydrofuran

Cited by 11 publications

References 43 publications

Delineating The Multiple Roles of B(C6F5)3 in the Chemoselective Deoxygenation of Unsaturated Polyols

Delineating The Multiple Roles of B(C6F5)3 in the Chemoselective Deoxygenation of Unsaturated Polyols

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Unprotected Carbohydrates as Starting Material in Chemical Synthesis: Not Just a Challenge but an Opportunity

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Delineating The Multiple Roles of B(C₆F₅)₃ in the Chemoselective Deoxygenation of Unsaturated Polyols

Delineating The Multiple Roles of B(C₆F₅)₃ in the Chemoselective Deoxygenation of Unsaturated Polyols