192764-31-1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 192764-06-0 N-Benzyl-N-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine 
• 100-58-3 phenylmagnesium bromide 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 

Downstream Products

• 215171-12-3 (4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 215171-14-5 (4R,5S)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 215171-13-4 (4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 223134-87-0 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 
• 192764-33-3 tert-butyl [(1R,2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamate 
• 161759-90-6 (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 188200-11-5 (2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 

Relevant academic research and scientific papers

Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2- O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and α- hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.

Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

The stereoselective addition of Grignard reagents to α-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols.