A highly efficient and versatile synthesis of D- and L-erythro-sphinganine

Hertweck, C.; Sebek, P.; Svatoš, Aleš

doi:10.1055/s-2001-18784

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A highly efficient and versatile synthesis of D- and L-erythro-sphinganine

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Hertweck, C., Sebek, P., & Svatoš, A. (2001). A highly efficient and versatile synthesis of D- and L-erythro-sphinganine. Synlett, (12), 1965-1967. doi:10.1055/s-2001-18784.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-10FC-9

Abstract

An expedient convergent synthesis of naturally occurring C-18-erythro-sphinganine (dihydrosphingosine, 1) is presented. Chiral protected 2-amino-1,3,4-butanetriol 6 is readily transformed into oxazolinyl oxirane building block 9, which is alkylated by a copper mediated S(N)2 type nucleophilic substitution with tetradecyl-magnesium chloride, This method promises to be suited for large-scale syntheses and for rapid access to sphinganine analogues modified in the backbone.