135968-95-5

Upstream product

• 108342-85-4 1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose 
• 108342-87-6 tetra-O-pivaloyl-β-D-galactopyranosylamine 
• 552-89-6 2-nitro-benzaldehyde 
• 108342-86-5 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide 

Downstream Products

• 1438284-43-5 (2E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-5-(o-nitrophenyl)-pent-2-enal 
• 135866-01-2 (1R)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(2-nitrophenyl)-3-butene 
• 135865-86-0 (1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(2-nitrophenyl)-3-butene 
• 108342-90-1 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-{[(R)-cyano-(2-nitro-phenyl)-methyl]-amino}-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 108365-45-3 4-fluoro-N-(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)-D-phenylglycinotrile 

Relevant academic research and scientific papers

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.

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