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. 2021 Jul 29;22(15):8171. doi: 10.3390/ijms22158171

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© 2021 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

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Scheme 4 — Synthesis of 14Z-1-deoxy-sphingosine-d₂ (25). Reagents and conditions: (a) vinylmagnesium bromide (1 M in THF), THF, −20 °C-r.t., 4 h; (b) TBLAH, EtOH, −78 °C, 3 h; (c) 10-bromo-1-decene, p-benzoquinone (10 mol%), Grubbs 2nd generation cat. (10 mol%), d-chloroform, 40 °C, 12 h; (d) D₂, 10% Pd/C, d-acetic acid (cat.), d-Methanol, r.t., 14 h; (e) 2,2-dimethoxypropane, p-TsOH (cat.), toluene, reflux, 2 h; (f) (i) 1-pentyne, tert-BuLi, THF, −78 °C, (ii) 22, HMPA, THF, −78 °C- r.t.,12 h; (g) H₂, Lindlar cat., EtOAc, DMF, r.t., 16 h; (h) AcCl, MeOH, 0 °C-r.t., 2 h.