92506-78-0Relevant articles and documents
Synthesis of N- and side chain protected aspartyl and glutamyl aldehyde derivatives. Reinvestigation of the reduction of Weinreb amides
Paris, Marielle,Pothion, Catherine,Heitz, Annie,Martinez, Jean,Fehrentz, Jean-Alain
, p. 1341 - 1344 (1998)
The reduction of Weinreb amides was reinvestigated in order to find conditions that will allow the synthesis of protected aspartyl and glutamyl aldehydes derivatives useful for peptide and pseudopeptide syntheses. We have demonstrated that lithium tris(te
Synthesis of threo-β-aminoalcohols from aminoaldehydes via chelation-controlled additions. Total synthesis of l-threo sphingosine and safingol
Jung, Michael E.,Yi, Sung Wook
supporting information; experimental part, p. 4216 - 4220 (2012/08/29)
Chelation-controlled addition of organocuprates to N-carbamoyl aminoaldehydes, prepared from functionalized amino acids, generated predominately the threo-β-amino alcohol derivatives through chelation with the carbamoyl moiety. The carbamate group is a stronger chelating group than other potentially good chelators, for example ethers, esters, thioethers, and gives good diastereoselectivity with cuprates. Thus addition of lithium divinylcuprate to the aldehyde generated from the serine derivative 25 in the presence of extra copper for chelation afforded the threo compound 26 in 83% yield. Cross-metathesis and cleavage of the protecting groups furnished l-threo sphingosine 21. In addition the lyso-sphingolipid protein kinase C inhibitor, safingol, 22, was prepared from commercially available O-benzyl N-BOC serine 28 in six steps and 56% overall yield by this method.
Synthesis of tetrahydro-β-carbolines and studies of the Pictet-Spengler reaction
Ducrot, Pierre,Rabhi, Cherif,Thal, Claude
, p. 2683 - 2692 (2007/10/03)
Tetrahydro-β-carbolines have been prepared in a diastereomerically pure form by a short, efficient synthetic sequence consisting of reaction of α- aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the