82722-22-3Relevant academic research and scientific papers
A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen(Co)III(OAc) catalysts
Savle, Prashant S.,Lamoreaux, Marika J.,Berry, John F.,Gandour, Richard D.
, p. 1843 - 1846 (1998)
Non-racemic terminal long-chain alkyl epoxides are prepared from racemic epoxides and 1 mol% (R,R)- and (S,S)-salen(Co)III catalysts following a modified procedure for kinetic resolution. The ee's for all epoxides (C-10, C-12, C-14, C-16, C-18, C-20) exceed 95% and the chemical yields range from 85% to 95%.
Asymmetric synthesis of (+)-passifloricin A and its 6-epimer
Chandrasekhar,Rambabu,Reddy, A. Syamprasad
, p. 4476 - 4478 (2008/09/21)
Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in ～5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction.
Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides
Lafont, Dominique,Bouchu, Marie-Noelle,Girard-Egrot, Agnes,Boullanger, Paul
, p. 181 - 194 (2007/10/03)
Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air | water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air | water interface; their π-A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing.
An efficient and stereoselective synthesis of (2R,2′S)-1-O-(2′-hydroxyhexadecyl)glycerol and its oxo analogs: Potential antitumour compounds from Shark Liver Oil
Baskaran, Subramanian,Baig, Mirza Hamed A.,Banerjee, Sharmila,Baskaran, Chitra,Bhanu, Kanchinadham,Deshpande, Sonali P.,Trivedi, Girish K.
, p. 6437 - 6452 (2007/10/03)
Reproducible, high-yielding, cost efficient, regio- and stereoselective synthesis of the title compound 3 isolated from Shark Liver Oil has been described. The compound 3 is prepared in an overall yield of 41% from chiral synthon 4 by the sequential reaction of 4 with C-13 Wittig salt; hydrogenation; epoxidation and regioselective opening. The oxo analogs 18 and 19 are prepared from four different achiral synthons by the sequential regioselective opening of the corresponding epoxide with different alcohols, methylation and deprotection strategies. Copyright
