Synthesis of phenyl 2-azido-2-deoxy-1-selenoglycosides from glycals

Santoyo‐González, Francisco; Calvo‐Flores, Francisco G.; Garcia‐Mendoza, P.; Hernández-Matéo, Fernando; Isac‐García, Joaquín; Robles‐Diaz, R.

doi:10.1021/jo00074a048

Cited by 74 publications

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“…exploited this methodology to access functionalized glycoside derivatives (Scheme a) . The same transformation on similar glycols was published only months apart by Santoyo‐González and co‐workers (Scheme b) …”

Section: Enol Substratesmentioning

confidence: 96%

Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry

Lauriers

Legault

2016

Asian J Org Chem

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This reviewisd edicated to Prof. Jean Lessard on the occasion of his 80th birthday Asian Abstract: In numerous iodine(III)-mediated methodologies that involve ketone compounds, the enol tautomer is expected to be the reactive species. In this context,t he exploration of enol and ynol surrogates as substrates is of great interest. Activated p-systems have been shown to exhibit interesting and highly exploitable behavior towardh ypervalent iodine reagents. This has led to the development of nu-merousu seful oxidativet ransformations. Enamines, enamides, enol derivatives, haloalkenes, and haloalkynes are all enol or ynol surrogates that are reactivet owards the most populari odanes and iodonium salts. This Focus Review will describep ast and on-going research involving these substrates to gain insighti nto the similarities and disparities observed in their reactivity profiles.The ORCID identification number(s) for the author(s) of this articlecan be found under http://dx.Scheme4.Proposed mechanism to explain 2 H-arizine formation and acetoxylation.Scheme5.Synthesis of 2-trifluoromethyloxazoles developed by Du, Zhao, and co-workers.Scheme6.Dichlorination of enaminesd evelopedbyZ hao, Du, and co-workers.Scheme7.Optimizedreductive conditionst oconvertthe dihaloimines to their corresponding enamines.

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Section: Enol Substratesmentioning

confidence: 96%

Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry

Lauriers

Legault

2016

Asian J Org Chem

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“…Although it is possible to use glycosyl nitrates directly for glycosidations [45], they usually have to be transformed into suitable glycosyl donors. To overcome this problem, an interesting azidophenylselenylation has been developed [46][47][48]. Now, sodium azide is oxidized by (diacetoxyiodo)benzene to the corresponding radical, which adds regioselectively to glycals like tri-O-acetyl-d-galactal (2b) (Scheme 7).…”

Section: Addition Of Nitrogen-centered Radicalsmentioning

confidence: 99%

Addition of Heteroatom Radicals to endo-Glycals †

Linker

2020

Chemistry

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Radical reactions have found many applications in carbohydrate chemistry, especially in the construction of carbon–carbon bonds. The formation of carbon–heteroatom bonds has been less intensively studied. This mini-review will summarize the efforts to add heteroatom radicals to unsaturated carbohydrates like endo-glycals. Starting from early examples, developed more than 50 years ago, the importance of such reactions for carbohydrate chemistry and recent applications will be discussed. After a short introduction, the mini-review is divided in sub-chapters according to the heteroatoms halogen, nitrogen, phosphorus, and sulfur. The mechanisms of radical generation by chemical or photochemical processes and the subsequent reactions of the radicals at the 1-position will be discussed. This mini-review cannot cover all aspects of heteroatom-centered radicals in carbohydrate chemistry, but should provide an overview of the various strategies and future perspectives.

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“…Similar methods for the synthesis of 2 -azido sugars using radical addition to glycals are the azidochlorination 21 and the azidophenylselenation. 22,23 Another possibility for the synthesis of organic azides is the diazo transfer using trifl yl azide. 24 In contrast to the methods described above, not the entire azido group is incorporated into a molecule but an N 2 moiety is transferred onto an existing amine under retention of confi guration.…”

Section: Synthesis Of Azide -Containing Carbohydratesmentioning

confidence: 99%

Azides in Carbohydrate Chemistry

Beckmann

Wittmann

2009

Organic Azides

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I )~.THF.HiO.N~ 2) NB, ~ TI-F . EIOH '''' Schcm c 16.7 SyntheSiS of aminoglycoside derivative 11 using azides as protecting groups for amines. First the amino groups of 18 were converted into azides by diazo /r.lnsfer. l1 After chemical remodeling of the aminoglycoside (one amino group was replaced by a hydroxy grotlp), the amines were regenerated by Stiludinger reduction" 474 Organic Azides: Sylllheses and Applicalions 23 BnO~O BnO~ N °9N'O~N' , 0 0 :1 ~ Cl Y 25 Cl PM~ (1.3 equiv), THF, H~, NaOH 46% PMe3 (1.

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Synthesis of phenyl 2-azido-2-deoxy-1-selenoglycosides from glycals

Cited by 74 publications

References 0 publications

Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry

Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry

Addition of Heteroatom Radicals to endo-Glycals †

Azides in Carbohydrate Chemistry

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