134699-92-6Relevant articles and documents
An improved glycal diazidation protocol with copper catalysis
Cao, Ruidi,He, Huan,Zhang, Chao,Liu, Xiao-Yu,Qin, Yong
, (2021)
A new and efficient copper-catalyzed glycal diazidation method is described that resulted in the generation of 2,3-diazido sugar acid derivatives. Compared to previously known protocols, the present approach demonstrated improved reaction yields and substrate scopes, thereby allowing for access to potential anti-viral agents.
Useful sialic acid modifications catalyzed by palladium
Chang, Chih-Wei,Norsikian, Stephanie,Beau, Jean-Marie
body text, p. 5195 - 5199 (2009/12/22)
A stereo- and regioselective allylic substitution on simple N-acetylneuraminic acid (Neu5Ac2en) derivatives that ensures the control of the regio- and stereoselectivity and affords the C-2 or C-4 products with high efficiency, was studied. The Neu5Ac2en substrates were easily prepared from the peracetylated methyl ester 9 obtained by standard treatment overnight of the corresponding Neu5Ac methyl ester. Treatment of acetate 10 under Pd0-catalyzed allylic substitution conditions using sodium dimethylmalonate as a nucleophile failed to provide any alkylation product. The regioselectivity was largely improved to a synthetically useful level when using a more basic monophosphine ligand. A complete reversal of the regioselectivity occurred when the reaction was performed in the presence of bidentate phosphine. Selective transformations of these products provide easy entry to a variety of modified sialic acid derivatives, which can serve as useful sialyl building blocks for biological research.
