776313-98-5Relevant articles and documents
Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
, p. 11023 - 11028 (2014/03/21)
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
Synthesis of fused oxa-aza spiro sugars from D-glucose-derived δ-lactone as glycosidase inhibitors
John Pal,Gupta, Preeti,Suman Reddy,Vankar, Yashwant D.
scheme or table, p. 6957 - 6966 (2011/02/28)
Four conformationally constrained fused oxa-aza spiro sugars have been synthesized from perbenzylated D-gluconolactone involving C-glycosylation of ketoses by using Me3SiCN, ring-closing metathesis, and diastereoselective dihydroxylation as key
Synthesis and elaboration of functionalised carbohydrate-derived spiroketals
Van Hooft, Peter A. V.,Oualid, Farid El,Overkleeft, Herman S.,Van der Marel, Gijsbert A.,Van Boom, Jacques H.,Leeuwenburgh, Michiel A.
, p. 1395 - 1403 (2007/10/03)
The scope of a stereoselective three-step approach for the synthesis of sugar derived spiroketals is presented. The methodology consists of Grignard addition of vinyl- or allylmagnesium bromide to a carbohydrate lactone, followed by K-10 clay mediated gly
A novel general route for the synthesis of C-glycosyl tyrosine analogues.
Brenna, Elisabetta,Fuganti, Claudio,Grasselli, Piero,Serra, Stefano,Zamboti, Sabrina
, p. 1872 - 1878 (2007/10/03)
A general method for the synthesis of C-glycosyl amino acids is described here. The stereoisomerically pure tyrosine analogues alpha-L-4 and beta-L-6 are prepared in reasonable overall yields from allyl derivatives 10 and 11. The key step is a benzannulation procedure which is employed in the creation of the aromatic ring that bears the amino acid function.
Replacement of an anomeric hydroxyl group by a halogen atom using PdCl2/Et3SiH/halogen source system
Hassan,El-Husseiny
, p. 803 - 811 (2007/10/03)
The anomeric hydroxyl group of perbenzylated and peracetylated carbohydrates can be stereoselectively replaced by a bromine or iodine atom using palladium dichloride, triethylsilane and carbon tetrabromide and/or iodine at room temperature. To illustrate the synthetic potential of this novel method, some models of O- and C-glycosides are reported. Reduction of sugar halide using excess of triethylsilane was not successful.
A novel and flexible synthesis of pyranose spiroacetal derivatives
Van Hooft, Peter A. V.,Leeuwenburgh, Michiel A.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Van Boeckel, Constant A. A.,Van Boom, Jacques H.
, p. 6061 - 6064 (2007/10/03)
A three-step approach to chiral pyranose [5,4], [5,5], [5,6] and [5,7] unsaturated spiroacetal derivatives from perbenzylated glucopyranolactone 1 is presented. The strategy involves Grignard addition of vinyl or allyl magnesium bromide to 1 to give 2 and
The synthesis of some epoxyalkyl β-C-glycosides as potential inhibitors of β-glucan hydrolases
Best, Wayne M.,Ferro, Vito,Harle, Julia,Stick, Robert V.,Tilbrook, D. Mathew G.
, p. 463 - 472 (2007/10/03)
The treatment of tetra-O-benzyl-D-glucono-1,5-lactone with various alkenylmagnesium halides gave the intermediate lactols which, upon reduction (Et3SiH/BF3) and protecting group manipulation, yielded alkenyl tetra-O-acetyl-β-D-C-gluc
