Guivisdalsky, Pedro N. published the artcileAn efficient stereocontrolled route to both enantiomers of platelet activating factor and analogs with long-chain esters at C-2: saturated and unsaturated ether glycerolipids by opening of glycidyl arenesulfonates, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Journal of Organic Chemistry (1989), 54(19), 4643-8, database is CAplus.
Both enantiomers of various ether/ester glycerophosphocholines (R)-I and (S)-II (R1 = e.g., hexadecyl, R2 = pentadecyl, Me), including platelet activating factor I (R1 = hexadecyl, R2 = Me), were synthesized from arenesulfonate derivatives of glycidol (R)- and (S)-III (R3 = C6H4Me-4, C6H4NO2-3) readily available in high enantiomeric purity. Regio- and stereospecific opening of (R)- or (S)-III with 1.0-1.4 equiv of long-chain saturated or unsaturated alc. using BF3.Et2O as catalyst in CH2Cl2 or CHCl3 afforded (R)- and (S)-R3SO3CH2CH(OH)CH2OR4 (IV; R3 = C6H4Me-4, C6H4NO2-3; R4 = oleyl, petroselinyl, hexadecyl) in 73-83% yields and with the same very high optical purity of the parent glycidyl arenesulfonate (94-99% enantiomeric excess). For saturated alkyl/acyl I and II O-benzylation of IV was achieved with retention of the arenesulfonte group by using benzyl trifluoromethanesulfonate in the presence of excess 2,6-di-tert-butyl-4-methylpyridine; the C-2 hydroxyl of unsaturated O-alkyl IV is protected as the methoxymethyl ether under mild conditions in which the arenesulfonate group is retained. Displacement of the arenesulfonate group and introduction of the phosphocholine group to produce PAF analogs complete this route to chiral ether-ester phospholipids.
Journal of Organic Chemistry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.
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