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Platelet-activating factor analogs. II. Synthesis of the 1-O-(4-decyloxymethylphenyl)- and 1-O-(4-decyloxyphenylmethyl) analogs

โœ Scribed by R.C. Anderson; B.E. Reitter; C.M. Winslow


Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
472 KB
Volume
39
Category
Article
ISSN
0009-3084

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โœฆ Synopsis


1-O-(4-Decyloxymethylphenyl)-and 1-O-(4-decyloxyphenylmethyl)-2-O-acetyl-glycero-3phosphorylcholine were synthesized from 2,2-dimethyl-l,3-dioxolane-4-methanol. The utility of a 2-O-tetrahydropyranyl ether as a protecting group and its facile removal in the pre~nce of a 3-phosphorylcholine is illustrated.


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The total synthesis of 1-O-alkyl-2-acetyl-3-glyceryl-(2-trimethyl ammoniummethyl)phosphonate, the phosphono analogue of 1-O-alkyl-2-acetyl-sn-glyceryl-3-phosphorylcho~ne, is described. The phosphonolipid shows much lower activity than the phospholipid stimulating serotonin release from rabbit platel

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The chemical synthesis of the amide analogs of 1-O-alkyl-2-O-acet yl-glyceryl-3-O-phosphoryl cholinc as its phosphono analog (phosphono-AGEPC)and 1-O-alkyl-2-O-acetyl-glyceryl-3-Ophosphoryl ethanolamine as its phosphono analog (phosphono-AGEPE) is reported. The intermediate acetamides for the subse