Synthesis of phosphatidylcholines containing ricinoleic acid

1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields, The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final...

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Published inTetrahedron Vol. 57; no. 51; pp. 10219 - 10227
Main Authors Borsotti, G, Guglielmetti, G, Spera, S, Battistel, E
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 17.12.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OH-protection
ricinoleic acid
FATTY-ACID
glycero-phosphocholine
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Summary:1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields, The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only beta -methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphochofine), respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)01057-2