<i>N</i>-(Phenylthio)-ε-caprolactam:  A New Promoter for the Activation of Thioglycosides

Durón, Sergio G.; Polat, Tülay; Wong, Chi‐Huey

doi:10.1021/ol0400084

Cited by 87 publications

(40 citation statements)

References 17 publications

(15 reference statements)

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“…The benzylidene-protected glycosyl thioglycoside 6 was not activated by NIS/ TfOH, [20] AgOTf/PhSCl, [21] nor N-(phenylthio)-ε-caprolactam/Tf 2 O [22] even at room temperature (Scheme 2) and was recovered unchanged under these reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

N‐Benzyl‐2,3‐trans‐Carbamate‐Bearing Glycosyl Donors for 1,2‐cis‐Selective Glycosylation Reactions

2010

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Glycosyl donors for the preparation of 1,2‐cis glycosides of amino sugars have been developed. The 2,3‐trans‐cyclic‐carbamate‐carrying glycosyl donors were readily prepared from the corresponding known trichloroethyl carbamate protected amino sugars under standard hydroxy group benzylation conditions. The donors exhibit high 1,2‐cis stereoselectivity towards secondary hydroxy group substrates. In the case of primary hydroxy acceptors, high stereoselectivities were achieved with the aid of the dioxane effect. After glycosylation, the carbamate was removed under alkaline conditions. Importantly, these glycosyl donors can be used in polymer‐supported and solid‐phase synthesis.

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Section: Resultsmentioning

confidence: 99%

N‐Benzyl‐2,3‐trans‐Carbamate‐Bearing Glycosyl Donors for 1,2‐cis‐Selective Glycosylation Reactions

2010

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“…[73] Commercially available 1-fluoropyridinium triflates successfully promoted the transformation of thioglycosides into O-glycosides. [74] In the past decade, organosulfur compounds have become valuable promoters for thioglycoside activation: Early studies were devoted to sulfonium or sulfenyl triflates, such as DMTST, MeSOTf, and PhSOTf; more recently, sulfenamide activators in combination with Lewis acids such as EtSNPhthTrB(C 6 F 5 ) 4 [75] and N-(phenylthio)-e-caprolactam-Tf 2 O [76] were proposed. Sulfinates in combination with Tf 2 O have also received much attention as thioglycoside activators.…”

Section: Thioglycosidesmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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“…[2,10,22,23] While no actual comparisons between the BSP and Ph 2 SO methods of thioglycoside activation have been carried out in this study, other work from our laboratory leads us to agree with the conclusion of van Boom and co-workers. [24][25][26][27] We anticipate that between BSP, its analogs introduced here, the recent modification of Wong (23), [28] and diphenyl sulfoxide, a reagent will be found to activate almost all classes of thioglycoside, in conjunction with trifluoromethanesulfonic anhydride, under milder conditions than have hitherto been possible. [29][30][31] 2.…”

mentioning

confidence: 99%

Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*

Crich

Banerjee

et al. 2005

Journal of Carbohydrate Chemistry

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An improved protocol for the large scale production of 1-benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1-benzenesulfinyl pyrrolidine and N,N-diethyl benzenesulfinamide function analogously to 1-benzenesulfinyl piperidine in the trifluoromethanesulfonic anhydride-mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at −78 °C as opposed to the −60 °C required to keep 1-benzenesulfinyl piperidine in solution. N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride which is attributed to its greater steric bulk.

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N-(Phenylthio)-ε-caprolactam: A New Promoter for the Activation of Thioglycosides

Cited by 87 publications

References 17 publications

N‐Benzyl‐2,3‐trans‐Carbamate‐Bearing Glycosyl Donors for 1,2‐cis‐Selective Glycosylation Reactions

N‐Benzyl‐2,3‐trans‐Carbamate‐Bearing Glycosyl Donors for 1,2‐cis‐Selective Glycosylation Reactions

New Principles for Glycoside‐Bond Formation

Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*

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