135865-85-9

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 108342-87-6 tetra-O-pivaloyl-β-D-galactopyranosylamine 
• 108342-86-5 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide 

Downstream Products

• 1196447-22-9 C₄₁H₅₉N₂O₁₃P 
• 1438284-38-8 (2E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-5-(p-nitrophenyl)-pent-2-enal 
• 1438284-52-6 (S)-8-(p-nitrophenyl)azocan-2-one 
• 135865-76-8 2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose 
• 135866-00-1 (1R)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-nitrophenyl)-3-butene 
• 135865-84-8 (1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-nitrophenyl)-3-butene 
• 108342-89-8 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-{[cyano-(4-nitro-phenyl)-methyl]-amino}-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 108342-89-8 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-{[(S)-cyano-(4-nitro-phenyl)-methyl]-amino}-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 108342-89-8 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-{[(R)-cyano-(4-nitro-phenyl)-methyl]-amino}-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 

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.

High diastereoselective vinylogous Mannich reaction induced by O-pivaloylated d-galactosylamine as the chiral auxiliary: Stereoselective synthesis of 8-arylazocan-2-one

The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl 3 as a promoter in THF. (S)-8-(p-Nitrophenyl) azocan-2-one can be stereoselective synthesized from (S) ethyl 7-galactosylamino-7-(p-nitrophenyl) hepta-2,4-dienoate by sequential hydrogenation of the double bond, cyclic lactam formation, and removal of the N-glycosidic auxiliary under basic conditions.

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.