121784-63-2

Upstream product

• 108342-85-4 1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose 
• 108342-86-5 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide 
• 104-88-1 4-chlorobenzaldehyde 
• 108342-87-6 tetra-O-pivaloyl-β-D-galactopyranosylamine 

Downstream Products

• 1196447-27-4 C₄₁H₅₉ClNO₁₁P 
• 108392-76-3 (R)-(p-Chlorophenyl)glycine hydrochloride 
• 848978-60-9 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-chlorophenyl)-4-(trifluoromethanesulfonyloxy)-4,5-didehydro-piperidine 
• 122294-60-4 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-[2-(4-chloro-phenyl)-4-methyl-3,6-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 122294-60-4 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-[2-(4-chloro-phenyl)-4-methyl-3,6-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 135865-97-3 (1R)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-chlorophenyl)-3-butene 
• 130887-57-9 (1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-chlorophenyl)-3-butene 
• 141330-73-6 Diethyl 4-chloro-α-<(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino>benzylphosphonate 
• 141330-78-1 Diethyl 4-chloro-α-<(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)amino>benzylphosphonate 
• 141330-77-0 Diethyl 4-chloro-α-<(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino>benzylphosphonate 
• 141330-79-2 Diethyl 4-chloro-α-<(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)amino>benzylphosphonate 
• 122294-62-6 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-[2-(4-chloro-phenyl)-4,5-dimethyl-3,6-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 122294-62-6 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-[2-(4-chloro-phenyl)-4,5-dimethyl-3,6-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 108365-46-4 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-D-phenylglycinotrile 

Relevant academic research and scientific papers

Diastereoselective Synthesis of Adjacent P,C-Stereogenic β-N-Glycosidic Linked α-Aminophosphinates

The diastereoselective formation of adjacent P,C-stereogenic β-N-glycosidic linked α-aminophosphinates is developed in high yields via a phospha-Mannich reaction. The reaction was performed by employing (Rp)-O-(?)-menthyl H-phenylphosphinate and O-pivaloylated N-galactosylimine for double stereodifferentiation and BF3·Et2O as a promoter in THF. O-Pivaloylated N-galactosylphenyl imine 2 and (Rp)-O-(?)-menthyl H-phenylphosphinate 1 were converted to N-galactosyl α-aminoalkylphosphinate 3 with ratios of diastereomers up to 20:1. The synthetic method of the conversion provides a rapid access to adjacent P,C-stereogenic chiral α-aminophosphinates.

Stereoselective synthesis of α-amino(phenyl)methyl(phenyl)phosphinic acids with O-pivaloylated D-galactoslamine as chiral auxiliary

Stereoselective synthesis of α-amino (phenyl)methyl(phenyl)phosphinic acids with O-pivaloylated D-galactosylamine as chiral auxiliary, was reported. 2 3 drops of acetic acid were added to a solution of amine 1 and aldehyde 2 in 2-propanol and the mixture was stirred at room temperature for about 0.5 h. A solution of N-galactosylaldimines 3 in THF was cooled to 0°C, and phosphinate 4 and SnCl4 were added. The mixture was stirred for 2 d at room temperature. The aqueous phase was extracted with CHCl3 and the organic layers were dried with anhydrous MgSO4, filtered, and concentrated in vacuo to yield the crude products. A solution of compound 5 in dry methanol was treated with freshly prepared solution of HCl. Then methanol was evaporated in vacuo and the remaining residue dissolved in 0.5 M HCl and extracted with pentane. The results revealed that AlCl3, SnCl 4, and BF3.OEt2 were able to promote the addition.

Palladium-catalysed C-C coupling reactions in the enantioselective synthesis of 2,4-disubstituted 4,5-dehydropiperidines using galactosylamine as a stereodifferentiating auxiliary

Stereoselective synthesis of enantiomerically pure 2,4-disubstituted piperidine derivatives, which are considered interesting pharmacophoric structures, was achieved starting with a tandem Mannich-Michael reaction sequence on O-pivaloylated N-galactosyl a

Carbohydrates as Chiral Templates: Stereoselective Strecker Synthesis of D-α-Amino Nitriles and Acids Using O-Pivaloylated D-Galactosylamine as the Auxiliary

The asymmetric synthesis of N-galactosyl D-α-amino nitriles is accomplished by application of 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosylamine (4) as the stereodifferentiating template in Strecker reactions.Aldimines 6 derived from 4 and aromatic or ali

Hetero-Diels-Alder Reactions on a Carbohydrate Template: Stereoselective Synthesis of (S)-Anabasin

Diastereoselective aza-Diels-Alder reaction using the tetra-O-pivaloyl-β-D-galactopyranosylamine as the chiral template affords the synthesis of enantiomerically pure 2-substituted piperidine derivatives, e.g. the tobacco alkaloid (S)-anabasin.