162221-36-5Relevant articles and documents
Facile synthetic route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivatives, the key intermediates for HIV protease inhibitors
Lei, Lijun,He, Xuchang,Bai, Donglu
, p. 1535 - 1540 (2007/10/03)
A facile and efficient route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivative (4S,5S)-4-benzyl-5-hydroxymethyl oxazolidin-2-one is presented. N-phthaloyl protected L-phenylalanine 1 was treated with thionyl chloride followed by hydroge
Stereocontrolled synthesis of anti-α-hydroxy-β-amino and anti-α,β-diamino acid derivatives by epoxidation of 1-arylthio-1-nitroalkenes
Ambroise, Lydia,Dumez, Estelle,Szeki, Andrea,Jackson, Richard F. W.
, p. 2296 - 2308 (2007/10/03)
Epoxidation of 1-tolylthio-1-nitroalkenes containing an allylic Boc-protected amino group yields cis-oxazolidinones 13, formed by intramolecular trapping of the presumed intermediate epoxides by the carbamate group. Epoxidation of the analogous Z- or Fmoc-protected derivatives yields the corresponding syn-epoxides which, although they cannot be isolated, can be trapped with aqueous ammonia, or more efficiently benzylamine, to give stereoisomerically pure anti-α,β-diamino acid derivatives.
A concise synthesis of aza-dipeptide isosteres
Faessler, Alex,Bold, Guido,Steiner, Heinz
, p. 4925 - 4928 (2007/10/03)
Aza-dipeptide isosteres as potent HIV-protease inhibitors containing a (hydroxyethyl)-hydrazine moiety are synthesised in >98% diastereomeric and enantiomeric purity starting from (L)-phenylalanine aldehyde.
Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research
G?hring, Wolfgang,Gokhale, Surendra,Hilpert, Hans,Roessler, Felix,Schlageter, Markus,Vogt, Peter
, p. 532 - 537 (2007/10/03)
The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.
Enantiomerically pure 3-amino-2-hydroxy and 5-amino-4-hydroxy acids from D-isoascorbic acid
Melon, D.,Gravier-Pelletier, C.,Merrer, Y. Le,Depezay, J. C.
, p. 585 - 593 (2007/10/02)
The chirospecific synthesis of 3-amino-2-hydroxy aldehyde or acid units is an important issue in the context of synthetic strategies directed towards the construction of biologically relevant target molecules such as amino sugars, antibiotics, enzyme inhi
