GaCl3-Catalyzed addition of thiols to glycals: a facile synthesis of 2-deoxy thioglycosides

Yadav, J. S.; Reddy, B. V. Subba; Bhasker, E. Vijaya; Raghavendra, S.; Narsaiah, A. Venkat

doi:10.1016/j.tetlet.2006.11.103

Cited by 28 publications

(6 citation statements)

References 36 publications

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“…The well‐documented effect of triphenylphosphane hydrogen bromide (TPHB) in favoring 1,2‐addition of alcohols to glycals (rather than Ferrier rearrangement) has also been demonstrated for 1,2‐addition of thiols to glycals leading to 2‐deoxythioglycosides 118a. The same effect, favoring 1,2‐addition over Ferrier rearrangement, has also been reported for ceric(IV) ammonium nitrate (CAN),221 and GaCl 3 222…”

Section: Other Nucleophiles In the Frmentioning

confidence: 67%

Recent Developments in the Ferrier Rearrangement

et al. 2013

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Glycals (1,2‐unsaturated, cyclic carbohydrate derivatives) readily undergo (catalyzed) substitution reactions at C‐1 accompanied by allylic rearrangement. This reaction, currently named Ferrier rearrangement, or the Ferrier I reaction, has established itself as a useful synthetic tool for carbohydrate transformations. By means of this reaction, glycals can be converted into highly useful 2,3‐unsaturated glycosides. This review summarizes recent developments in the use of promoters for the Ferrier rearrangement of O‐, N‐, C‐ and S‐nucleophiles with glycals.

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Section: Other Nucleophiles In the Frmentioning

confidence: 67%

Recent Developments in the Ferrier Rearrangement

et al. 2013

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“…8 Likewise, similar procedures also include the formation of 2-chloro-2-deoxyglycoside and subsequent radical dechlorination, 9 as well as the preparation of 2-deoxy-2-phenylthio-glycoside followed by the reduction of Raney Nickel. 10 Previous reports indicated that acid-catalyzed addition to glycals represents the most direct method that can be operated under various conditions, including hydrogen bromide, 11 triphenylphosphine hydrogenbromide, 12 Dowex-50 [H þ ] in the presence of LiBr, 13 CeCl 3 $7H 2 O/NaI, 14 LaCl 3 $7H 2 O/NaI, 15 TMSOTfeNEt 3 , 16 BCl 3 (or BBr 3 ), 17 ceric ammonium nitrate, 18 GaCl 3 ,19 and Rhenium(V) [ReOCl 3 (SMe 2 )(OPPh 3 )]. 20 We recently applied microwave-assisted glycosylation of hex-1-en-3-uloses to synthesize a-2-deoxyulosides.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis

et al. 2011

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“…Rearrangement catalyzed by FeCl 3 based ionic liquid has been described in which the ionic liquid has proved to be an efficient reaction medium, playing a dual role of a catalyst as well as that of a solvent [39]. Recently, GaCl 3 was reported as an efficient catalyst for the addition of thiols to glycals under extremely mild conditions, affording 2-deoxy thioglycosides in high yields with a good ␣-selectivity [40]. Ceric ammonium nitrate was also reported to mediate the synthesis of 2-deoxy-1-thioglycosides, being the 2,3-unsaturated-S-glycosides obtained only as minor reaction products [41].…”

Section: Introductionmentioning

confidence: 99%