Synthesis of phosphatidylcholines containing ricinoleic acid

Autor:	Silvia Spera, Gianfranco Guglielmetti, Gianpietro Borsotti, Ezio Battistel
Rok vydání:	2001
Předmět:	chemistry.chemical_compound Chemistry Castor oil Organic Chemistry Drug Discovery Ricinoleic acid medicine Organic chemistry Chloroformate Protecting group Biochemistry Chloride medicine.drug
Zdroj:	Tetrahedron. 57:10219-10227
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)01057-2
Popis:	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 β-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-phosphocholine), respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9d801190281a0556d8cc5c698fe2278d https://doi.org/10.1016/s0040-4020(01)01057-2 Zobrazit plný text záznamu Full Text from ScienceDirect