400888-39-3

Upstream product

• 150942-98-6 t-butyl lithioacetate 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 5292-43-3 bromoacetic acid tert-butyl ester 

Downstream Products

• 1092835-09-0 C₄₃H₅₀O₈ 
• 903881-98-1 benzyl (3,7-anhydro-4,5,6,8-tetra-O-benzyl-3-cyano-2-deoxy-D-glycero-L-manno-oct)onate 
• 903881-97-0 benzyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 
• 400888-52-0 methyl (3,7-anhydro-4,5,6,8-tetra-O-benzyl-3-cyano-2-deoxy-D-glycero-L-manno-oct)onate 
• 400888-43-9 methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 
• 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 
• 903882-00-8 benzyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-oct]onate 
• 184100-33-2 ((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid 
• 849472-65-7 (S)-4-(2-((2S,3R,4S,5R,6R)-2-benzamido-3,4,5-tris(acetoxy)-6-acetoxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(9-fluorenylmethoxycarbonylamino)butanoic acid 
• 849472-72-6 (S)-2-tert-Butoxycarbonylamino-4-[2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-2-benzoylamino-tetrahydro-pyran-2-yl)-acetylamino]-butyric acid tert-butyl ester 

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.

A new Co(0) complex mediated synthesis of C-glycoside analogues

Properly protected glyconolactones, readily available from the parent sugars, react under mild conditions with α-bromoacetates in the presence of a soluble Co(0) complex, either in stoichiometric or substoichiometric amounts, to give a Reformatsky-type addition product to the lactone. The addition product can be subsequently converted into a variety of compounds: dehydroxylation with triethylsilane in the presence of boron trifluoride affords C-glycosides.

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