213828-83-2Relevant articles and documents
Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling
Dondoni, Alessandro,Mariotti, Giandomenico,Marra, Alberto
, p. 4475 - 4486 (2007/10/03)
A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of α- or β-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-α-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of α- and β-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.
General, stereoselective synthesis of ethylene isosteres of α- and β- glycosylasparagines
Dondoni, Alessandro,Mariotti, Giandomenico,Marra, Alberto
, p. 3483 - 3487 (2007/10/03)
The coupling of α- or β-D-linked lithium C-glycosyl acetylides with N- Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded α- and β-anomer pairs of C-glycosyl α-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd.
Design and use of an oxazolidine silyl enol ether as a new homoalanine carbanion equivalent for the synthesis of carbon-linked isosteres of O- glycosyl serine and N-glycosyl asparagine
Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
, p. 933 - 944 (2007/10/03)
A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the α-amino acid side chain at the anomeric carbon of sugars. This new functio
Synthesis of ethylene isosteres of β-D-galactosyl- and β-D-glucosyl- L-asparagine
Dondoni, Alessandro,Massi, Alessandro,Marra, Alberto
, p. 6601 - 6604 (2007/10/03)
The Mukaiyama-type coupling of galactosyl and glucosyl aldehydes with a four-carbon atom silyl enol ether carrying the oxazolidine ring affords the corresponding sugar containing aldols (65-74%) that upon deoxygenation and oxidative cleavage of the hetero
