134450-46-7

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 147770-27-2 (2S,3R)-2-Amino-4,4-difluoro-1,6-diphenyl-hexan-3-ol 
• 72155-45-4 Boc-L-phenylalaninal 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 147770-26-1 N-t-butyloxycarbonyl-(1,6-diphenyl-3,3-difluoro-4(R,S)-hydroxy-5(S)-amino-hexane) 
• 147770-25-0 ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester 

Downstream Products

• 134450-34-3 2S-(N-Benzyloxycarbonyl-valinyl)amino-3-oxo-4,4-difluoro-1,6-diphenyl-hexane 

Relevant academic research and scientific papers

Highly efficient synthesis of 2(S)-3(R,S)-2-amino-4,4-difluoro-1,6-diphenyl-3-hydroxyhexane - the key intermediate for a series of potent HIV proteinase inhibitors

Many α,α-difluoroketones such as 2S-(N-benzyloxycarbonyl-valinyl)amino-3-oxo-4,4-difluoro-1,6-diphenyl-hexane (1), with the strongly electronegative fluorines next to the carbonyl group, are usually fully hydrated.As a result of the hydration of the carbonyl group, the difluoroketones can act as transition-state analog inhibitors of certain proteinases.Reformatsky reaction of aldehyde N-t-butyloxycarbonyl L-phenylalaninal (3), with bromodifluoromethylphenylacetylene provided the key intermediate for the synthesis of a series of potent HIV proteinase inhibitors exemplified by 1. - Keywords: Synthesis; Aminodifluorodiphenylhydroxyhexane; HIV proteinase inhibitors; NMR spectroscopy; Mass spectrometry