Phosphocholine-like derivatives of some steroids via their 1,2-cyclic monoalkyl-rac-glycerothiophosphates
✍ Scribed by Stephan D. Stamatov; Salo Gronowitz
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- English
- Weight
- 497 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
1,2-cyclic 3-O-ethyl-and 3-O-hexadecyl-rac-glycerothiophosphates of dehydroisoandrosterone, 13-sitosterol and cholesterol were used as synthons for the preparation of derivatives of phosphocholine and a homologue by alkylation with trimethylamine and triethylamine. The reaction was accomplished either at room temperature (20~25°C) or on moderate heating (70~90°C) to give the target steryl-3-S- [2-(methylene-oxyalkyl)-2-(N,N,N-trialkylammonium) ethyl-l-O-] phosphates and their steryl-3-O-thiophosphate analogues in yields ranging from 30% to 80%. The reaction offers a novel pathway for the synthesis of unknown phospholipid structures.