Synthesis of C-glycosyl amino acids: scope and limitations of the tandem Tebbe/Claisen approach

Add time:09/09/2019    Source:sciencedirect.com

Amino acids may be used as coupling partners for esterification with 3-hydroxy glycals as substrates for the tandem Tebbe/Claisen approach to the synthesis of C-glycosyl amino acids. Whilst esters of substituted α-amino acids do not successfully undergo Tebbe, or other, methylenation, esters of β- or γ-amino acids are methylenated to yield vinyl ethers, which then undergo smooth thermal rearrangement to yield β-C-glycoside products. tert-Butyl esters are found to be unreactive to the Tebbe reagent, and as such tert-butyl protection may be used for other carboxylic acids.

We also recommend Trading Suppliers and Manufacturers of N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester (cas 13726-84-6). Pls Click Website Link as below: cas 13726-84-6 suppliers

Prev:First total synthesis and determination of the absolute configuration of 1-N-methyl-3-methylamino-[N-butanoicacid-3-(9-methyl-8-propen-7-one)-amide]-benzo[f][1,7]naphthyridine-2-one, a novel benzonaphthyridine alkaloid
Next:Diastereoselective [3+2]-photocycloaddition of chiral 1,4-naphthalenedicarboxylic esters to alkenes)