Synthesis of Sphingolipids with an ω-Esterified Long Acyl Chain, Ceramide Components of the Human Epidermis

Takuya TASHIRO; Kenji MORI

doi:10.1271/bbb.120333

Organic Chemistry Regular Papers

Synthesis of Sphingolipids with an ω-Esterified Long Acyl Chain, Ceramide Components of the Human Epidermis

Takuya TASHIRO, Kenji MORI

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Keywords: ceramide, olefin cross metathesis, epidermis, sphingolipid, stratum corneum

JOURNAL FREE ACCESS

2012 Volume 76 Issue 9 Pages 1715-1720

DOI https://doi.org/10.1271/bbb.120333

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Abstract

Esterified ceramides, (2S,3R,4E)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol (2) and (2S,3R,4E,6R)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3,6-triol (4), are minor components of the human stratum corneum. We synthesized these ceramides by employing olefin cross metathesis as the key reaction for constructing their ω-hydroxytriacontanoyl part (13).

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