400888-52-0

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 400888-43-9 methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 400888-39-3 ((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester 

Downstream Products

• 903882-03-1 methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate 

Relevant academic research and scientific papers

Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions

γ-Sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from d-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting β-cyano esters provides C-ketoside-based γ-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides.

Synthesis of sugar-fused GABA-analogs

γ-Aminobutyric acid (GABA)-sugar analogs in the form of C-ketosides can be prepared in 4 to 7 steps starting from D- or L-Glucono- and D-Galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl-trifluoromethanesulfonate (TMS-OTf) promote