165683-83-0

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 165683-81-8 (2S,3S)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 
• 192764-07-1 N-Benzyl-N-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine 
• 188200-13-7 (2S,3S)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-3-phenyl-1,2-propanediol 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 165683-86-3 (1S,2S)-N-tert-butoxycarbonylamino-3-tert-butyldimethylsilyloxy-2-mesyloxo-1-phenyl-1-propylamine 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 681125-79-1 (2R,3S)-3-phenyl-3-(tert-butoxycarbonylamino)-2-(1-ethoxyethoxy)propionic acid 
• 174283-00-2 tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate 
• 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 
• 154130-21-9 methyl (S,S)-2-acetoxy-3-tert-butoxycarbonylamino-3-phenylpropionate 
• 215171-16-7 Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl ester 
• 174282-99-6 (2R,3S)-1-tert-butyldimethylsilyloxy-3-tert-butoxycarbonylamino-2-p-nitrophenylcarbonyloxy-3-phenylpropane 

Relevant academic research and scientific papers

Stereocontrolled synthesis of all four stereoisomers of fully protected 2-amino-3-hydroxypentanoic acid from imines derived from D-glyceraldehyde

N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective phenylmagnesium bromide addition to afford the corresponding aminodiols, whose absolute configuration at the newly formed stereogenic carbon depends on the

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.

An enantioselective, stereodivergent approach to anti- and syn-α-hydroxy-β-amino acids from anti-3-amino-1,2-diols. Synthesis of the ready for coupling Taxotere side chain

Both anti- and syn-α-hydroxy-β-amino acids are efficiently synthesised in protected form and high enantiomeric purity from readily available anti-N-Boc-1-tert-butyldimethylsilyl-3-amino-1,2-diols. The preparation of the anti series is straightforward, and

A convenient, stereodivergent approach to the enantioselective synthesis of N-Boc-aminoalkyl epoxides

An efficient, stereodivergent and enantioselective synthesis of N-Boc-aminoalkyl epoxides has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-diols, and after a change in the nitrogen protecting group, an intramol