126409-25-4Relevant articles and documents
Transition-state mimetics for HIV protease inhibitors: Stereocontrolled synthesis of hydroxyethylene and hydroxyethylamine isosteres by ester- derived titanium enolate syn and anti-aldol reactions
Ghosh,Fidanze
, p. 6146 - 6152 (2007/10/03)
Stereocontrolled syntheses of hydroxyethylene dipeptide isostere and aminoalkyl epoxides for hydroxyethylamine isosteres are described. The stereochemistry of both stereogenic centers of the aminoalkyl epoxides 10 and 15 as well as they γ-lactone 17 was assembled by our recently developed highly selective ester-derived titanium enolate aldol reactions. The Ti- enolate of 6 reacted with (benzyloxy)acetaldehyde and cinnamaldehyde to provide the syn-aldol product 7 and anti-aldol product 12, respectively. Removal of the chiral template followed by Curtius rearrangement of the resulting acid provided the desired amine functionality. The present syntheses represent practical and enantioselective entry to a range of other dipeptide isosteres, which are not limited to amino acid derived substituents.
A Stereoselective Method for the Preparation of HIV-1 Protease Inhibitors Based on the Lewis Acid Mediated Reaction of Allylsilanes and N-Boc-α-amino Aldehydes
D'Aniello, Fabiana,Taddei, Maurizio
, p. 5247 - 5250 (2007/10/02)
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An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors
Ghosh, Arun K.,McKee, Sean P.,Thompson, Wayne J.
, p. 6500 - 6503 (2007/10/02)
An efficient and stereocontrolled synthesis of hydroxyethylene dipeptide isosteres 1 from commercially available, optically pure D-mannose is described.This synthesis represents a practical and enantioselective entry to a range of other dipeptide isostere