192764-33-3

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 188200-11-5 (2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 
• 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 
• 192764-31-1 (2S,3R)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-3-phenyl-1,2-propanediol 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 215171-12-3 (4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 259748-03-3 (1R,2S)-N-tert-butoxycarbonylamino-3-tert-butyldimethylsilyloxy-2-mesyloxo-1-phenyl-1-propylamine 
• 161759-90-6 (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 223134-87-0 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 
• 215171-13-4 (4R,5S)-5-Hydroxymethyl-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 
• 90643-25-7 (2S,3R)-3-amino-3-phenylpropane-1,2-diol hydrochloride 

Relevant academic research and scientific papers

Cysteine protease inhibitors

of the formula (IV): where: R1=R′C(O), R′SO2, R′=a bicyclic, saturated or unsaturated, 8-12 membered ring system containing 0-4 hetero atoms selected from S, O and N, which is optionally substituted with up to four substituents independently selected from groups a), b) and c) below; or R′=a monocyclic, saturated or unsaturated, 5-7 membered ring containing 0-3 hetero atoms selected from S, O and N, which monocyclic ring bears at least one substituent selected from group a) and/or c) and which may optionally bear one or two further substituents selected from group b); R4=H, C1-7-alkyl, Ar-C1-7-alkyl, Ar, C3-7-cycloalkyl; C2-7alkenyl; R3=C1-7-alkyl, C2-C7 alkenyl, C2-C7 alkenyl, C3-7-cycloalkyl, Ar-C1-7-alkyl, Ar; R5=C1-7-alkyl, halogen, Ar-C1-7-alkyl, C1-3-alkyl-CONR3R4 or a bulky amine R6 is H, C1-7-alkyl, Ar-C1-7-alkyl, C1-3-alkyl-SO2-Rix, C1-3-alkyl-C(O)—NHRix or CH2XAr q is 0 or 1 have utility as inhibitors of cysteine proteases such as cathepsin K and falcipain.

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.