287962-67-8

Upstream product

• 287962-74-7 (R)-4-[(S)-3-((2R,3S,4R,5R,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-hydroxy-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 10583-64-9 2-Acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranose 
• 443916-48-1 (R)-4-[3-((2R,3S,4R,5R,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-hydroxy-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 443916-54-9 (R)-4-[3-((2R,3S,4R,5R,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-hydroxy-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 287962-79-2 4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-L-gluco-oct-1-ynitol 
• 443916-17-4 7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undecitol 

Relevant academic research and scientific papers

Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling

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 Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge.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

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.