1454884-16-2

Upstream product

• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 532-20-7 D-arabinofuranose 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 
• 1454884-08-2 tert-butyl (4R,5S,6R,E)-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylidenehept-2-enoate 

Relevant academic research and scientific papers

Asymmetric syntheses of the methyl glycosides of 2-deoxy-2-aminohexoses: D-allosamine, D-mannosamine, D-idosamine and D-talosamine

A range of the methyl glycosides of 2-deoxy-2-aminohexoses, comprising D-allosamine, D-mannosamine, D-idosamine and D-talosamine, were prepared from the corresponding D-aldopentoses via a seven step synthetic sequence. The doubly diastereoselective conjugate addition of the requisite antipode of lithium N-benzyl-N-(α-methylbenzyl)amide and in situ enolate oxidation with the requisite antipode of camphorsulfonyloxaziridine (CSO) was used as the key, stereodefining step. Sequential reduction of the resultant α-hydroxy-β-amino esters and oxidative cleavage of the C(1)–C(2) diol unit furnished the corresponding α-amino aldehydes. Subsequent N- and O-deprotection gave the target compounds (as mixtures of anomers) in good yield and high diastereoisomeric purity.

Asymmetric syntheses of dihydroxyhomoprolines via doubly diastereoselective lithium amide conjugate addition reactions

The asymmetric syntheses of novel dihydroxyhomoprolines have been achieved using the doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a set of four chiral α,β-unsaturated esters (derived from d-pentoses) as one of the key steps. A full account of the diastereoselectivity observed in these conjugate additions is presented and the stereochemical outcomes of these reactions have been established unambiguously via a combination of hydrogenolytic chemical correlation and single crystal X-ray diffraction analyses. A tandem hydrogenolysis/intramolecular reductive amination reaction was then used to create the corresponding enantiopure pyrrolidines, providing access to (2′S,3′S,4′R)-dihydroxyhomoproline and (2′S,3′R, 4′S)-dihydroxyhomoproline after deprotection.