10550-58-0Relevant articles and documents
Stereospecific synthesis of 2-substituted ether phospholipids
Bhatia,Hajdu
, p. 16 - 20 (1989)
-
Homologues and isomers of noladin ether, a putative novel endocannabinoid: Interaction with rat cannabinoid CB1 receptors
Appendino, Giovanni,Ligresti, Alessia,Minassi, Alberto,Daddario, Nives,Bisogno, Tiziana,Di Marzo, Vincenzo
, p. 43 - 46 (2003)
Two regioisomers and 13 analogues of the putative endocannabinoid noladin ether (2-arachidonyl glyceryl ether, 2-AGE, 1) were synthesized and tested for their interaction with CB1 receptors in rat brain membranes. The results showed that a C-20 tetra-unsaturated moiety is necessary for high affinity, and that a series of alkyl glyceryl ethers of potential occurrence in brain tissues have less affinity than 2-AGE for CB1 receptors.
ENANTIOMERE DER 2,2'-DINITROBIPHENYL-6,6'-DICARBONSAEURE ALS STEREOSELEKTIV WIRKSAME, REVERSIBLE SCHUTZGRUPPEN-II. STEREOSELEKTIVE SYNTHESEN VON LIPIDGRUNDKOERPERN ODER -BAUSTEINEN
Mueller, H. K.,Burgold, J.
, p. 1533 - 1538 (1986)
S-(-)-1,1'-diphenyl-2,2'-dinitro-6,6'-dicarboxylic acid (1) is used as an axial-chiral protecting group for the primary hydroxy group of glycerol and glycerol derivatives.Diesters of 1 were formed which have the largest distance between the nitro groups and the nucleophilic substituents on glycerol.After hydrogenolytical removal of the protecting group asymmetric glycerol derivatives were obtained with approximately 10percent enantiomeric excess.Hydroxybromination of 12 resulted mainly in he anti-Markovnikov 13a instead of the Markovnikov product 13b expected, which was present only in traces.This deviation is discussed.
Sarcoglycosides A-C, new O-glycosylglycerol derivatives from the South China sea soft coral Sarcophyton infundibuliforme
Li, Liang,Wang, Chang-Yun,Shao, Chang-Lun,Guo, Yue-Wei,Li, Guo-Qiang,Sun, Xue-Ping,Han, Lei,Huang, Hui,Guan, Hua-Shi
experimental part, p. 1495 - 1502 (2009/10/17)
Chemical examination of the soft coral Sarcophyton infundibuliforme collected from the South China Sea resulted in the isolation of the three new O-glycosylglycerol derivatives sarcoglycosides A-C (1 - 3), together with two known compounds, chimyl alcohol
Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
Stamatov, Stephan D.,Stawinski, Jacek
, p. 3787 - 3800 (2008/10/09)
A trifluoroacetate-catalyzed opening of the oxirane ring of glycidyl derivatives bearing allylic acyl or alkyl functionalities with trifluoroacetic anhydride (TFAA), provides an efficient entry to configurationally homogeneous 1(3)-acyl- or 1(3)-O-alkyl-sn-glycerols. Selective introduction of tert-butyldimethylsilyl- (TBDMS), or triisopropylsilyl- (TIPS) transient protections at the terminal sites within these key intermediates secures 1(3)-acyl- or 1(3)-O-alkyl-3(1)-O-TBDMS (or TIPS)-sn-glycerols as general bifunctional precursors to 1,2(2,3)-diacyl-, 1(3)-O-alkyl-2-acyl- and 1,3-diacyl-sn-glycerols and hence triester isosters. Incorporation of a requisite acyl residue at the central carbon of the silylated synthons with a subsequent Et3N·3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment at the stereogenic C2-centre of the monosilylated glycerides; (ii) replacement of the silyl moiety by a short- or long-chain carboxylic acid residue by means of the acylating agent: tetra-n-butylammonium bromide (TBABr)-carboxylic acid anhydride (CAA)-trimethylsilyl bromide (TMSBr); and (iii) removal of the trichloroacetyl replacement, provides pure 1,3-diacyl-sn-glycerols. The TBABr-CAA-TMSBr reagent system allows also a one-step conversion of 1,2-diacylglycerol silyl ethers into homochiral triglycerides with predefined asymmetry and degree of unsaturation. These compounds can also be accessed via a two-step one-pot approach where the trichloroacetyl derivatives of 1,2(2,3)- or 1,3-diacyl-sn-glycerols serve as triester building blocks for establishing the third ester bond at preselected C3(1)- or C2-positions within the glycerol skeleton at the very last synthetic stage. In all instances, the target compounds were produced under mild conditions, in high enantiomeric purity, and in practically quantitative yields. The Royal Society of Chemistry 2007.
