A High Yield Synthesis of Phosphatidyl Ethanolamines Using Phosphoramidite Intermediates

Autor:	Bernadette Swords, Christopher McGuigan
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Phosphoramidite Aqueous solution Dinitrogen tetroxide Organic Chemistry Ethanolamines Medicinal chemistry Chloride Catalysis chemistry.chemical_compound chemistry medicine Aliphatic compound Tetrahydrofuran Alkyl medicine.drug
Zdroj:	Synthesis. 1993:133-136
ISSN:	1437-210X 0039-7881
Popis:	Alkyl 2-aminoethyl hydrogen phosphates (phosphatidyl ethanolamines) were prepared via phosphoramidite chemistry. tert-butoxy-carbonyl N-protection of 2-aminoethanol, followed by cyclisation with phosphorus(III) chloride gave the phosphoramidite 3-tert-butoxycarbonyl-2-chloro- 1,3,2-oxazaphospholidine (3). This reacted with long chain alcohols (C6 to C18) to give 2-alkyloxy-3-tert-butoxvcarbonyl-1,3,2-oxazaphospholidines 4a-d which were oxidised to 2-alkyloxy-3-tert-butoxycarbonyl-2-oxo-1,3,2-oxaza-phospholidines 5a-d with dinitrogen tetroxide. Simultaneous heterocycle cleavage and N-deprotection were achieved with refluxing aqueous tetrahydrofuran, to give the target 2-aminoethyl phospates
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0bc1b2c6cbbf2ec73535bba083c5b91e https://doi.org/10.1055/s-1993-25816 Zobrazit plný text záznamu