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Iodocyclofunctionalization of (Z)-1-Trichloroacetimidoyloxyalk-2-enes and 3-Trichloroacetimidoyloxyalk-1-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate and (+/-)-threo-Sphinganine Triacetate

DOI: 10.1039/P19860001339

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1339 - 1344 (1986)

Update date:2022-08-05

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Authors:

Bongini, AlessandroBongini, Alessandro

Cardillo, GiulianaCardillo, Giuliana

Orena, MarioOrena, Mario

Sandri, SergioSandri, Sergio

Tomasini, ClaudiaTomasini, Claudia

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Article abstract of DOI:10.1039/P19860001339

(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihidro-oxazole.From this compound, two routes were developed, either to pure (+/-)-erythro-sphinganine triacetate or to pure (+/-)-threo-sphinganine triacetate, respectively.The neutral cleavage of 4-(1-iodohexadecyl)-2-trichloromethyl-4,5,-dihydro-oxazole gave the corresponding amide which, by treatment with Amberlyst A 26 (CO3(2-) form), afforded the cis-4-hydroxymethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazole together with a minor amount of cis-2-hydroxymethyl-3-pentadecylaziridine.After hydrolysis of the oxazole and full acetylation, (+/-)-erythro-sphinganine triacetate was obtained in 70 percent yield.On the other hand, acidic cleavage of the 4-(1-iodohexadecyl)oxazole 2-amino-3-iodo-octadecan-1-ol hydrochloride, which was directly treated with Amberlyst A 26 (AcO(-) form).The product was acetylated and (+/-)-threo-sphinganine triacetate was recovered in 70 percent yield after chromatographic separation.As an alternative, 3-trichloroacetimidoyloxyoctadec-1-ene was cyclized with N-iodosuccinimide to give a 20:80 cis:trans mixture of 4-iodomethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazoles.After ring cleavage, the corresponding ring-opened hydrochlorides were obtained.The mixture was then treated with Amberlyst A 26 (AcO(-) form) and the product was directly acetylated.After silica gel chromatography, (+/-)-threo-sphinganine triacetate and (+/-)-erithro-sphinganine triacete were obtained in good yield, in the ratio 80:20.

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Product name:(2S,3R)-2-Amino-octadecane-1,3-diol; hydrochloride

Cas No:111168-12-8

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