Efficiency of cadmium carbonate as an aryl glycosidation catalyst: Effects of lot variations on product compositions

Dick, Wolfgang

doi:10.1016/s0008-6215(00)87111-6

Cited by 12 publications

(6 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was suggested that the generated cadmium bromide was the actual activator, but cadmium bromide by itself was ineffective, similar to Helfrich’s observations made with mercuric cyanide activation . Later, it was also confirmed that the product composition depends on the surface area of cadmium carbonate …”

Section: Glycosyl Bromidesmentioning

confidence: 79%

“…However, cadmium chloride by itself was ineffective, similar to Helferich’s explanation for mercuric cyanide activation . As discussed in Section , the product composition also in this case depends on the surface area of cadmium carbonate …”

Section: Glycosyl Chloridesmentioning

confidence: 91%

“…In another study, the authors successfully applied tin triflate-promoted activation of glycosyl chloride donors ( vide infra ) . Dick has reported activation of glycosyl bromides in the presence of lead(II) carbonate, wherein a moderate yield (37%) for the synthesis of tetra-acetylated α,β-phenyl glucosides was obtained when per-acetylated glucosyl bromide was treated with PhOH in the presence of PbCO 3 …”

Section: Glycosyl Bromidesmentioning

confidence: 99%

“…239 Later, it was also confirmed that the product composition depends on the surface area of cadmium carbonate. 251 3.2.3. Activation with Group 13−15 Post-transition Metal Salts (Indium, Tin, Lead, or Bismuth).…”

Section: Activation With Mercury and Other Group 12mentioning

confidence: 99%

“…306 Dick has reported activation of glycosyl bromides in the presence of lead(II) carbonate, wherein a moderate yield (37%) for the synthesis of tetra-acetylated α,βphenyl glucosides was obtained when per-acetylated glucosyl bromide was treated with PhOH in the presence of PbCO 3 . 251 Recently, Demchenko and co-workers have shown an efficient activation of glycosyl halides in the presence of Bi(OTf) 3 . 308 Compared to most common metal salt activators of glycosyl halides wherein stoichiometric amount of activators is needed, a rapid activation of glycosyl bromides was achieved in the presence of 0.35 equiv of Bi(OTf) 3 .…”

Section: Activation With Mercury and Other Group 12mentioning

confidence: 99%

See 4 more Smart Citations

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

2022

View full text Add to dashboard Cite

Advances in synthetic carbohydrate chemistry have dramatically improved access to common glycans. However, many novel methods still fail to adequately address challenges associated with chemical glycosylation and glycan synthesis. Since a challenge of glycosylation has remained, scientists have been frequently returning to the traditional glycosyl donors. This review is dedicated to glycosyl halides that have played crucial roles in shaping the field of glycosciences and continue to pave the way toward our understanding of chemical glycosylation.

show abstract

Section: Glycosyl Bromidesmentioning

confidence: 79%

Section: Glycosyl Chloridesmentioning

confidence: 91%

Section: Glycosyl Bromidesmentioning

confidence: 99%

Section: Activation With Mercury and Other Group 12mentioning

confidence: 99%

Section: Activation With Mercury and Other Group 12mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

2022

View full text Add to dashboard Cite

show abstract

Cadmium Carbonate

Prabhakaran¹

2001

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Darstellung ungesättigter Kohlenhydrate durch Esterpyrolyse, II. Thermische cis‐Eliminierungen aus vollständig acetylierten Aldopyranosen

et al. 1982

View full text Add to dashboard Cite

Die Pentaacetate 1, 2, 7 und 9 der b-D-GIucose, a-D-Mannose, PD-Allose und PD-Galactose sowie die Tetraacetate 13 und 18 der b-o-Xylose und PD-Ribose, in Aceton gel8st. eliminieren in einer Stromungsapparatur bei Temperaturen um 350°C und Verweilzeiten von 0.5 -1 min regioselektiv und stereoselektiv die 1-0-Acetylgruppe. Die jeweiligen Anomeren mit trans-sttindigem Wasserstoff in 2-Position gehen entsprechend dem pericyclischem Eliminierungsmechanismus diese Reaktion nicht ein. Die prim& gebildeten 2,3,4,6-Tetra-O-acetyl-l,5-anhydro-hex-l-enite 3, (aus 1 oder 2), 8 und 10 sowie die 2,3,4-Tri-O-acetyl-1,5-anhydro-pent-l-enite 14 und 19 fuhren nachfolgend in einer [3,3]-sigmatropen Umlagerung zu den aoder b-Triacetyl-3-desoxy-hex-2enopyranosen 4 oder 5, 12 bzw. den aoder ~Triacetyl-3-desoxy-pent-2-enopyranosen 15 oder 16. Es erfolgt jeweils teilweise Anomerisierung, so von 12 zu 11. -Durch Umlagerung rnit nachfolgender Essigsaureanhydrid-Eliminierung werden aus 5 und 16 die Enone 6 bzw. 17 gebildet. -Die 1,2,4,0-Tetra-O-acetyI-3-desoxy-~~threo-hex-2-enopyranose (12) wird erstmalig beschrieben. Die 13C-NMR-Daten beweisen, daR sowohl 11 als auch 12 bevorzugt in einer Okf5(D)-Konformation vorliegen.

show abstract

Efficiency of cadmium carbonate as an aryl glycosidation catalyst: Effects of lot variations on product compositions

Cited by 12 publications

References 7 publications

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

Cadmium Carbonate

Darstellung ungesättigter Kohlenhydrate durch Esterpyrolyse, II. Thermische cis‐Eliminierungen aus vollständig acetylierten Aldopyranosen

Contact Info

Product

Resources

About