6734-79-8

Upstream product

• 13380-37-5 (2S,4R)-1-Methyl-4-propyl-pyrrolidine-2-carboxylic acid hydrazide 
• 161881-09-0 2-(bromomethyl)pent-1-ene 
• 50-00-0 formaldehyd 

Downstream Products

• 13380-39-7 methyl (2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxylate 
• 1146963-00-9 methyl 1,4,5,6,9-penta-O-benzyl-8,10-dideoxy-8-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-3-thio-D-ribo-β-L-gluco-dec-3-ulopyranoside 
• 1146962-98-2 methyl 2-O-acetyl-1,4,5,6,9-penta-O-benzyl-8,10-dideoxy-8-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-3-thio-D-ribo-β-L-manno-dec-3-ulopyranoside 
• 1146962-68-6 methyl 5,6,7,10-tetra-O-benzyl-2,3,9,11-tetradeoxy-9-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-4-thio-D-erythro-α-D-galacto-undec-4-ulopyranosidonitrile 
• 1146962-71-1 methyl {methyl 5,6,7,10-tetra-O-benzyl-2,3,9,11-tetradeoxy-9-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-4-thio-D-erythro-α-D-galacto-undec-4-ulopyranosid}onate 
• 1146962-44-8 phenyl 2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-6-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 1146962-45-9 4-chlorophenyl 2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-6-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 1146962-46-0 4-methoxyphenyl 2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-6-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 1146962-58-4 methyl 1-O-acetyl-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-7-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside 
• 1146962-89-1 methyl (1R)-1-O-acetyl-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-7-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside 
• 1146962-87-9 methyl (1S)-1-O-acetyl-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-7-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside 
• 148077-13-8 lincophenicol 

Relevant academic research and scientific papers

Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding

A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

Synthesis of 1,2,3-triazole analogues of lincomycin

In search for new antibiotics we replaced the amide moiety of lincomycin 1 by a 1,2,3-triazole ring. The 1,2,3-triazoles 10a-10k were obtained as single regioisomers by 'click reaction' of azide 5 with the alkyne 9k, derived from propyl hygric acid, and the alkyl, aryl, or cycloalkyl alkynes ribosomes 9a-9j. The new analogues proved inactive towards wild-type and A2058G mutant.