133333-28-5

Upstream product

• 178421-79-9 (4S,5S)-3-(tert-butoxycarbonyl)-5-cyanomethyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidine 
• 165683-87-4 (1S,2S)-1-(tert-butyldimethylsilyloxymethyl)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate 
• 165683-84-1 (2S,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-butanol 
• 104882-03-3 (2S,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-1,2-butanediol 
• 108868-54-8 (3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile 
• 107202-61-9 (2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane 

Downstream Products

• 101669-82-3 methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate 
• 132406-51-0 (4S,5S)-4-Cyclohexylmethyl-5-methoxycarbonylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Ready access to stereodefined β-hydroxy-γ-amino acids. Enantioselective synthesis of fully protected cyclohexylstatine

A convenient entry to enantiopure syn or anti β-hydroxy-γ-amino acids is described. The starting compounds for the synthesis, anti 3-amino-1,2-diols, are readily available in high enantiomeric purity through catalytic asymmetric epoxidation of an allylic alcohol and titanium-promoted oxirane opening. After adequate protection of the nitrogen, a stereodivergent sequence leads to both anti and syn N-Boc aminoalkyl epoxides. Subsequent regioselective ring-opening with cyanide, protection of the resulting secondary alcohol and nitrile to carboxyl conversion afford, in good yields, protected β-hydroxy-γ-amino acid belonging to either the anti (erythro) or syn (threo) series. This methodology has been applied to the enantioselective preparation of cyclohexylstatine, a key component of several aspartyl protease inhibitors, in fully protected form.