106930-52-3Relevant articles and documents
Preparative synthesis of β-amino alcohols from α-amino dicarboxylic acid derivatives
Kirillova, Yu. G.,Baranov,Prokhorov,Esipova,Shvets
, p. 1315 - 1317 (2009)
A low-expensive preparative procedure has been developed for the synthesis of protected β-amino alcohols from α-amino dicarboxylic acid derivatives.
Nanoaggregates of biodegradable amphiphilic random polycations for delivering water-insoluble drugs
Nottelet, Benjamin,Patterer, Manuela,Francois, Benjamin,Schott, Marc-Alexandre,Domurado, Martine,Garric, Xavier,Domurado, Dominique,Coudane, Jean
, p. 1544 - 1553 (2012)
Cationic amphiphilic random copolyesters were obtained by copolymerization of 5-Z-amino-δ-valerolactone and ε-caprolactone. The amino content of the final copolymers was controlled by the polymerization feed ratio and was in the range 10 to 100%. Copolymers solubility and aggregation behavior was assessed by conductometric and zeta potential analyses. A critical aggregation concentration of ca. 0.05% (w/v) was found for all water-soluble copolymers that formed nanoaggregates. Two populations were found to be present in equilibrium with hydrodynamic diameters in the range of 30-50 and 100-250 nm. The capacity to use the amphiphilic and cationic character of the nanoaggregates to encapsulate highly hydrophobic compounds was further investigated. Finally, copolymers hemo- and cytocompatibility were evaluated by hemagglutination, hemolysis, and cells proliferation tests. The results showed that the proposed cationic amphiphilic random copolyesters are biocompatible.
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.
