120255-31-4

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 108342-87-6 tetra-O-pivaloyl-β-D-galactopyranosylamine 

Downstream Products

• 178946-89-9 bis(3-indolyl)-4-chlorophenylmethane 
• 1380444-77-8 N-[(1-methylindol-3-yl)-4-chlorophenylmethyl]-(2,3,4,6-tetra-O-pivaloyl-β-D-galactosyl)amine 
• 1380444-76-7 N-[(1-methylindol-3-yl)-4-chlorophenylmethyl]-(2,3,4,6-tetra-O-pivaloyl-β-D-galactosyl)amine 
• 1380444-72-3 N-[(5-methoxyindol-3-yl)-4-chlorophenylmethyl]-(2,3,4,6-tetra-O-pivaloyl-β-D-galactosyl)amine 
• 1609945-85-8 cis-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactosyl)-(3R)-(4-chlorophenyl)aziridine-(2R)-ethyl formate 
• 1609945-93-8 ethyl (2S,3S)-2-amino-3-(4-methylphenylthio)-3-(4-chlorophenyl)propanoate 
• 1426683-90-0 (2R,3R)-2-isopropoxy-3-[(S)-4-chlorophenyl(2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamino)methyl]tetrahydro-2H-furan 
• 1426683-84-2 (2R,3R)-2-isopropoxy-3-[(S)-4-chlorophenyl(2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamino)methyl]tetrahydro-2H-pyran 
• 1426683-81-9 (2S,3R)-2-methoxy-3-[(S)-4-chlorophenyl(2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamino)methyl]tetrahydro-2H-pyran 
• 1287297-26-0 (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one 
• 848978-55-2 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-chlorophenyl)-5,6-didehydro-piperidin-4-one 

Relevant academic research and scientific papers

Lewis acid catalyzed diastereoselective vinylogous Mannich reaction induced by O-pivaloylated d-galactosylamine as the chiral auxiliary: Stereoselective synthesis of 6-arylpiperidin-2-ones

The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-aminocarbonyl derivatives, in the form of (S)-δ-amino-δ-arylpent-2-enoic ester, has been achieved in high yield via a vinylogous Mannich reaction, utilizing poly-O-pivaloylated

Asymmetric aza-Friedel-Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

The diastereoselective formation of β-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel-Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral templa

Highly efficient asymmetric vinylogous Mannich reaction induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

The diastereospecific formation of β-N-glycoside-linked α-amino-2(5H)-furanone has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and ZnCl2·Et 2O as a promoter in Et2O. Imines 3 of aromatic compounds and trimethylsiloxyfuran 4 were converted to N-galactosyl α-amino-2(5H)- furanone 5, giving ratios of diastereomers higher than 20:1. This procedure provides rapid access to biologically important γ-butenolide derivatives.

Stereoselective synthesis of bromopiperidinones and their conversion to annulated heterocycles

N-Galactopyranosyl- and N-glucopyranosyl imines of aliphatic, aromatic and heteroaromatic aldehydes react with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene in a domino Mannich-Michael reaction cascade to give 2-substituted 5,6-dehydro-piperidin-4-ones with high diastereoselectivity. Treatment of these cyclic enaminones with N-bromo-succinimide yields the corresponding 2-substituted 5-bromo-5,6-dehydropiperidinones which react with L-Selectride or methylcuprate to afford the saturated bromo-piperidinones with high diastereoselectivity. Condensation reactions of these products with thioamides afford thiazolopiperidines.

Glycosylation-induced and Lewis acid-catalyzed asymmetric synthesis of β-N-glycosidically linked α-aminophosphonic acids derivatives

The diastereospecific formation of β-N-glycosidically linked α-aminophosphonic acids derivatives has been achieved with high yield via a Mannich-type reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and boron trifluoride diethyl etherate as a catalyst in THF. Imines 3 of aromatic compounds and diethyl phosphite were converted to N-galactosyl α-aminoalkylphosphonate 4, giving ratios of diastereomers higher than 19:1. This procedure provides a rapid access to biologically important galactosyl α-aminophosphonic acids derivatives.