92905-04-9Relevant articles and documents
Syntheses of All Four Stereoisomers Which Are Conformationally Constrained 1,4-Dioxanyl Analogs of the Antineoplastic Ether Lipid ET-18-OCH3
Duclos, Richard I.,Makriyannis, Alexandros
, p. 6156 - 6163 (2007/10/02)
The syntheses of each of the four nearly optically pure stereoisomers of oxy>phosphocholine (2,3,2',3') were performed by two parallel divergent sequences.Phosphocholines 2 and 3 were prepared via the corresponding 5-heptadecyl-2-(hydroxymethyl)-1,4-dioxanes 21 and 23, respectively, from the completely regiospecific mixed-hydride reductions of (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane (19) and (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane (20), respectively.The two 4-heptadecyl-3,6,8-trioxabicyclooctanes 19 and 20 were the two separable products from an intramolecular cyclization reaction.By a parallel divergent sequence from the enantiomeric starting material, 3-O-benzyl-sn-glycerol (16'), the other two diastereomeric oxy>phosphocholines 2' and 3' were prepared.These four monocyclic oxy>phosphocholines (2,3,2',3') are conformationally constrained analogs of the antineoplastic and immunomodulatory ether lipid rac-2-O-methyl-1-O-octadecylglycero-3-phosphocholine (rac-1) (rac-ET-18-OCH3, rac-Edelfosine).
