188200-13-7

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 188200-12-6 Benzyl-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-amine 
• 131319-74-9 (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 
• 192764-07-1 N-Benzyl-N-[(S)-((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

• 2935-35-5 (S)-2-phenylglycine 
• 215171-16-7 Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl ester 
• 215171-17-8 Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester 
• 158830-39-8 methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 
• 165683-83-0 (2S,3S)-3-tert-butoxycarbonylamino-1-tert-butyldimethylsilyloxy-3-phenyl-2-propanol 
• 154130-21-9 methyl (S,S)-2-acetoxy-3-tert-butoxycarbonylamino-3-phenylpropionate 
• 165683-81-8 (2S,3S)-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.

Reversal of the stereochemical course of the addition of phenylmagnesium bromide to N-benzylimines derived from R-glyceraldehyde depending on the O-protecting group and its application to the synthesis of both enantiomers of phenylglycine

The N-Benzyl imines derived from 2,3-di-O-benzyl-D-glyceraldehyde and 2,3-di-O-isopropylidene-D-glyceraldehyde reacted with phenylmagnesium bromide to afford fully protected aminodiols with total diastereoselectivity. The stereochemical course of the addition reaction depends on the nature of the O-protecting group. These compounds can be easily transformed to enantiomerically pure (R) and (S)α-phenylglycine.

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.