506-03-6Relevant articles and documents
Raspailynes, Novel Long-Chain Acetylenic Enol Ethers of Glycerol from the Marine Sponges Raspailia pumila and Raspailia ramosa
Guella, Graziano,Mancini, Ines,Pietra, Francesco
, p. 1050 - 1062 (1987)
The sponges Raspailia pumila and R. ramosa (Demospongiae, Tetractinomorpha, Axinellida) from the North-East Atlantic are shown to contain a series of novel long-chain enol ethers of glycerol where the enol ether C=C bond is conjugated, in sequence, to both an acetylenic and an olefinic bond.Polar extracts give raspailynes hydroxylated at their (1Z,5Z)-1,5-alkadien-3-ynyl chain, like raspailyne A1 (=(+)-(S)-3--1,2-propanediol; (+)-2) and isoraspailyne A (=(+)-3--1,2-propanediol; (+)-3).Less polar extracts give 3 different types of raspailynes not hydroxylated at the chain.Raspailynes of the first type have either the (1Z,5Z)-configuration in a linear chain such as raspailyne B2 (=(-)-(S)-3--1,2-propanediol; (-)-4), raspailyne B1 (=(-)-3--1,2-propanediol; (-)-5), and raspailyne B (=3--1,2-propanediol; 6) or the (1Z,5Z)-configuration in a chain ending with an isopropyl group, like isoraspailyne B1 (=3--1,2-propanediol; 7) and isoraspailyne B (=3--1,2-propanediol; 8).Raspailynes of the second type have the (1Z,5E)-configuration, like isoraspailyne B1a (=3--1,2-propanediol; 9) and isoraspailyne Ba (=3--1,2-propanediol; 10).Raspailynes of the third type have the (1E,5Z)-configuration, like isoraspailyne B1b (=3--1,2-propanediol; 11).The (S)-configuration for (+)-1, (+)-2, and (-)-4 is derived from chemical correlations.
Platelet activating factor derivative and synthesis method thereof
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, (2017/08/29)
The invention belongs to the technical field of chemical synthesis and discloses a platelet activating factor derivative with a formula (I) structure, wherein a substituent group R refers to an acryl group. A synthetic route includes nine-step reaction by taking chiral source S-configuration solketal as a starting reactant. The method is adopted for synthesis of a 2-sulfo platelet activating factor and a derivative thereof for the first time and has advantages of high yield, easiness in separation and the like. Low-cost batch synthesis of 2-S-PAF and the derivative thereof is realized, and significances to activity research of 2-S-PAF and the derivative thereof, biological experiments, clinical application and disease treatment are achieved.
Chemoenzymatic synthesis of a focused library of enantiopure structured 1-O-alkyl-2,3-diacyl-sn-glycerol type ether lipids
Magnusson, Carlos D.,Gudmundsdottir, Anna V.,Haraldsson, Gudmundur G.
supporting information; experimental part, p. 1821 - 1836 (2011/04/17)
A highly efficient two-step chemoenzymatic synthesis of enantiopure structured ether lipids of the 1-O-alkyl-2,3-diacyl-sn-glycerol type has been developed. Chimyl, batyl and selachyl alcohols possessing pure saturated fatty acid (SFA) attached to the sn-3 position and pure EPA and DHA attached to the sn-2 position were obtained under full regiocontrol. This was offered by mild conditions and a highly efficient lipase that operated at room temperature. High-resolution 1H NMR spectroscopy was used to monitor the progress of the reactions and to evaluate the full regiocontrol of the reactions involved by keeping track of all prospective adducts involved in these reactions. This was extended to preparation of a focused library of eight monoacyl intermediate adducts for all even-numbered SFA ranging from C2-C16 and the corresponding EPA and DHA structured diacyl glycerol ethers (DAGE) products for chimyl, batyl and selachyl alcohols, the total of 72 compounds.
