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Chemical Structure| 15956-28-2 Chemical Structure| 15956-28-2
Chemical Structure| 15956-28-2

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Synonyms: Tetrakis(acetato)dirhodium(II); Rhodium(II) acetate dimer

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Product Citations

Product Citations

Singh, Surya Pratap ; Chaudhary, Umesh ; Sharma, Indrajeet ;

Abstract: Traditional glycosylation methods using thioglycosides often require harsh conditions or expensive metal catalysts. This study presents a more sustainable alternative by employing copper, an earth-abundant catalyst. We developed diazo-based thioglycoside donors that, through copper catalysis, undergo intramolecular activation to form glycosyl sulfonium ions, leading to the generation of oxocarbenium ions. This versatile approach efficiently accommodates a variety of O-nucleophiles, including primary, secondary, and tertiary, as well as complex bioactive molecules. It is compatible with various glycosyl donors and protecting groups, including superarmed, armed, and disarmed systems. Notably, the methodology operates orthogonally to traditional thioglycoside and alkyne donors and has been successfully applied to the orthogonal iterative synthesis of trisaccharides. Mechanistic insights were gained by studying the electronic effects of electron-donating (OMe) and electron-withdrawing (NO2) groups on the donors, offering a valuable understanding of the intramolecular reaction pathway.

Keywords: earth-abundant metals ; copper catalysis ; thioglycoside donor ; orthogonal reactivity ; iterative synthesis ; intramolecular activation

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Product Details of Dirhodium tetraacetate

CAS No. :15956-28-2
Formula : C8H12O8Rh2
M.W : 441.99
SMILES Code : CC1=OC23[Rh]45(O=C(C)O3)C6(O=C(C)O5)[Rh]2(O1)4O=C(C)O6
Synonyms :
Tetrakis(acetato)dirhodium(II); Rhodium(II) acetate dimer
MDL No. :MFCD00003538

Safety of Dirhodium tetraacetate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
 

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